Bipolar hosts for light emitting devices

ABSTRACT

Some embodiments provide a compound represented by Formula 1: 
     
       
         
         
             
             
         
       
     
     wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7  and R 8  are independently H, C 1 -C 3  alkyl, or C 1-3  perfluoroalkyl; HT is optionally substituted carbazoyl, optionally substituted phenylcarbazolyl, optionally substituted (phenylcarbazolyl)phenyl, optionally substituted phenylnaphthylamine, or optionally substituted diphenylamine; and ET optionally substituted benzimidazol-2-yl, optionally substituted benzothiazol-2-yl, optionally substituted benzoxazol-2-yl, optionally substituted 3,3′-bipyridin-5-yl, optionally substituted quinolin-8-yl, optionally substituted quinolin-5-yl, or optionally substituted quinoxalin-5-yl. Other embodiments provide an organic light-emitting diode device comprising a compound of Formula 1.

CROSS REFERENCE TO RELATED APPLICATIONS

This application claims the benefit of U.S. Provisional PatentApplication No. 61/735,478, filed Dec. 10, 2012, which is incorporatedby reference herein in its entirety.

BACKGROUND

1. Field

This invention relates to compounds for use in organic light emittingdiodes, such as for host materials.

2. Description of the Related Art

White organic light emitting devices (WOLEDs) have attracted muchattention and been intensively studied due to their potentialapplications as backlight sources, full color displays, and generallighting. Among various device configurations to produce white light, asingle-emissive-layer device employing phosphorescent materials incombination with proper host materials is desirable. Some advantages ofsuch a device may include reduced overall cost, increased quantumefficiency, and easier fabrication. Since phosphorescent emitters canharvest both singlet and triplet excitons, use of phosphorescentemitters in WOLEDs may lead to the potential of achieving 100% internalquantum efficiency. Adding host materials may also reduce concentrationquenching of the emissive materials and further increase the efficiency.In addition, adding host materials can reduce the required amount ofexpensive emissive material, and the fabrication of a single layerdevice is easier and more cost effective than a multiple layer device.As a result, the single-emissive-layer device with phosphorescent andhost materials can lower the overall cost of fabricating the WOLEDs.

SUMMARY

Some embodiments include a compound represented by Formula 1:

HT-Ph¹-Ph²-ET  (Formula 1)

wherein Ph¹ and Ph² are independently optionally substitutedo-phenylene; HT is optionally substituted phenylcarbazolyl, optionallysubstituted (phenylcarbazolyl)phenyl, optionally substituted4-(phenylnaphthylamino)phenyl, or optionally substituted4-(diphenylamino)phenyl; and ET is optionally substitutedbenzimidazol-2-yl, optionally substituted benzimidazol-2-ylphenyl,optionally substituted di(benzimidazol-2-yl)phenyl, optionallysubstituted benzothiazol-2-yl, optionally substitutedbenzothiazol-2-ylphenyl, optionally substituteddi(benzothiazol-2-yl)phenyl, optionally substituted benzoxazol-2-yl,optionally substituted benzoxazol-2-ylphenyl, optionally substituteddi(benzoxazol-2-yl)phenyl, optionally substituted 3,3′-bipyridin-5-yl,optionally substituted quinolin-8-yl, optionally substitutedquinolin-5-yl, or optionally substituted quinoxalin-5-yl.

Some embodiments provide a compound represented by Formula 2:

wherein R¹, R², R³, R⁴, R⁵, R⁶, R⁷ and R⁸, are independently H, C₁-C₃alkyl, or C₁₋₃ perfluoroalkyl; HT is optionally substituted carbazoyl,optionally substituted phenylcarbazolyl, optionally substituted(phenylcarbazolyl)phenyl, optionally substituted phenylnaphthylamine, oroptionally substituted diphenylamine; and ET is optionally substitutedbenzimidazol-2-yl, optionally substituted benzothiazol-2-yl, optionallysubstituted benzoxazol-2-yl, optionally substituted 3,3′-bipyridin-5-yl,optionally substituted quinolin-8-yl, optionally substitutedquinolin-5-yl, and optionally substituted quinoxalin-5-yl.

Some embodiments also include optionally substitutedN-phenyl-N-(4′″-(1-phenyl-1H-benzo[d]imidazol-2-yl)-[1,1′:2′,1″:2″,1′″-quaterphenyl]-4-yl)naphthalen-1-amine;optionally substituted9-phenyl-3-(4″-(1-phenyl-1H-benzo[d]imidazol-2-yl)[1,1′:2′,1″-terphenyl]-2-yl)-9H-carbazole;optionally substituted3-(3″,5″-bis(1-phenyl-1H-benzo[d]imidazol-2-yl)-[1,1′:2′,1″-terphenyl]-2-yl)-9-phenyl-9H-carbazole;optionally substituted2,2′-(2″-(9-phenyl-9H-carbazol-3-yl)-[1,1′:2′,1″-terphenyl]-3,5-diyl)bis(benzo[d]oxazole);optionally substituted3-(4″-(1-phenyl-1H-benzo[d]imidazol-2-yl)-[1,1′:2′,1″-terphenyl]-2-yl)-9-(p-tolyl)-9H-carbazole;or optionally substituted9-phenyl-3-(4′″-(1-phenyl-1H-benzo[d]imidazol-2-yl)-[1,1′:2′,1″:2″,1′″-quaterphenyl]-4-yl)-9H-carbazole.

These compounds can be used in light-emitting devices, e.g. as hostcompounds.

Other embodiments provide an organic light-emitting diode devicecomprising a cathode; an anode; a light-emitting layer disposed betweenand electrically connected to the anode and the cathode; ahole-transport layer between the anode and the light-emitting layer; andan electron-transport layer between the cathode and the light-emittinglayer; wherein at least one of the light-emitting layer, thehole-transport layer and the electron-transport layer comprise a hostcompound described herein.

Other embodiments provide an organic light-emitting diode devicecomprising: a cathode; an anode; and a light-emitting layer disposedbetween and electrically connected to the anode and the cathode; whereinthe light-emitting layer comprises a host compound described herein.

These and other embodiments are described in greater detail below.

BRIEF DESCRIPTION OF THE DRAWINGS

FIG. 1 is a schematic of a device incorporating an embodiment of acompound described herein.

FIG. 2 is a schematic of a device incorporating an embodiment of acompound described herein.

FIG. 3 is a current density versus voltage plot of an embodiment of thelight-emitting device incorporating an embodiment of a compounddescribed herein.

FIG. 4 is a current density versus voltage plot of an embodiment of thelight-emitting device incorporating an embodiment of a compounddescribed herein.

DETAILED DESCRIPTION

The use of effective host materials can be helpful in making efficientWOLEDs. A host may be improved if it transports both holes and electronsefficiently at the same speed. A host may also be improved if itstriplet energy is high enough to effectively confine the tripletexcitons on the guest molecules. Some host materials are a mixture ofhole-transport material and electron-transport material, which may posepotential problems such as phase separation, aggregation and lack ofuniformity, and unequal material degradation rates. Thus, development ofan ambipolar single molecule (i.e., a molecule capable of transportingboth holes and electrons effectively) for a host material would beuseful.

Some ambipolar single molecule hosts have been used in either singlecolor or white OLED device applications. However, these molecules haveeither unbalanced hole-transport and electron-transport properties, orthe devices made from these molecules have only moderate efficiency.

Thus, there is a need for a new type of ambipolar host that can beeasily synthesized, possesses high thermal and electrochemicalstability, and has well balanced hole-transport and electron-transportmobility when used as a host for phosphorescent emissive materials. Sucha host may be used to achieve a simple device structure with highquantum efficiency and low turn-on voltage.

Unless otherwise indicated, when a compound or chemical structuralfeature such as aryl is referred to as being “optionally substituted,”it includes a feature that has no substituents (i.e. unsubstituted), ora feature that is “substituted,” meaning that the feature has one ormore substituents. The term “substituent” has the broadest meaning knownto one of ordinary skill in the art, and includes a moiety that replacesone or more hydrogen atoms in a parent compound or structural feature.The term “replaces” is merely used herein for convenience, and does notrequire that the compound be formed by replacing one atom with another.In some embodiments, a substituent may be an ordinary organic moietyknown in the art, which may have a molecular weight (e.g. the sum of theatomic masses of the atoms of the substituent) of 15 g/mol to 50 g/mol,15 g/mol to 100 g/mol, 15 g/mol to 150 g/mol, 15 g/mol to 200 g/mol, 15g/mol to 300 g/mol, or 15 g/mol to 500 g/mol. In some embodiments, asubstituent comprises, or consists of: 0-30, 0-20, 0-10, or 0-5 carbonatoms; and 0-30, 0-20, 0-10, or 0-5 heteroatoms, wherein each heteroatommay independently be: N, O, S, Si, F, Cl, Br, or I; provided that thesubstituent includes one C, N, O, S, Si, F, Cl, Br, or I atom.

Examples of substituents include, but are not limited to, hydrocarbyl,such as alkyl, alkenyl, alkynyl; heteroalkyl, including any alkylwherein one or more heteroatoms replaces one or more carbon atoms, andsome accompanying hydrogen atoms (e.g. N replaces CH, O replaces CH₂, Clreplaces CH₃, etc.), such as alkoxy, alkylthio, haloalkyl, haloalkoxy,amino, etc.; heteroalkenyl, including any alkenyl wherein one or moreheteroatoms replaces one or more carbon atoms, and some accompanyinghydrogen atoms, such as acyl, acyloxy, thiocarbonyl, alkylcarboxylate,O-carbamyl, N-carbamyl, O-thiocarbamyl, N-thiocarbamyl, C-amido,N-amido, sulfinyl, isocyanato, isothiocyanato, etc; heteroalkynyl,including any alkynyl wherein one or more heteroatoms replaces one ormore carbon atoms, and some accompanying hydrogen atoms, such as cyano,thiocyanato, cyanato; aryl; heteroaryl; hydroxy; aryloxy; thiol; halo;S-sulfonamido; N-sulfonamido; nitro, silyl; sulfonyl;trihalomethanesulfonyl; trihalomethanesulfonamido; etc. In someembodiments, a substituent may be optionally substituted alkyl, —O-alkyl(e.g. —OCH₃, —OC₂H5, —OC₃H₇, —OC₄H₉, etc.), —S-alkyl (e.g. —SCH₃,—SC₂H₅, —SC₃H₇, —SC₄H₉, etc.), —NR′R″, —OH, —SH, —CN, —NO₂, or ahalogen, wherein R′ and R″ are independently H or optionally substitutedalkyl.

For convenience, the term “molecular weight” is used with respect to amoiety or part of a molecule to indicate the sum of the atomic masses ofthe atoms in the moiety or part of a molecule, even though it may not bea complete molecule.

The term benzimidazol-2-yl refers to the ring system:

The term “benzimidazol-2-ylphenyl” refers to the ring system:

The term “di(benzimidazol-2-yl)phenyl” refers to the ring system:

In some, the benzimidazol-2-yl may have a substituent group R⁷ as shownbelow:

wherein R⁷ is H, C₁-C₃ alkyl, or optionally substituted aryl, including,but not limited to phenyl and naphthyl. If R⁷ is phenyl, the ring systemcan be referred to as 1-phenylbenzimidazol-2-yl.

The term benzoxazol-2-yl refers to the ring system:

The term “benzoxazol-2-ylphenyl” refers to the ring system:

The term “di(benzoxazol-2-yl)phenyl” refers to the ring system:

The term benzothiazol-2-yl refers to the ring system:

The term “benzothiazol-2-ylphenyl” refers to the ring system:

The term “quinolin-8-yl” refers to the ring system:

The term “quinolin-5-yl” refers to the ring system:

The term “quinoxalin-5-yl” refers to the ring system:

The term “carbazolyl” refers to the ring system:

which includes, but is not limited to

wherein R′ can be independently H, optionally substituted C₁-C₃ alkyl,or C₁₋₃ perfluoroalkyl.

The term “phenylcarbazolyl” refers to the ring systems:

wherein R′ can be H, optionally substituted C₁-C₃ alkyl, or C₁₋₃perfluoroalkyl.

The term “phenylcarbazolylphenyl” refers to the ring system:

The term “4-(phenylcarbazolyl)phenyl” refers to the ring system:

The term “diphenylamine” refers to the ring system:

The term “phenylnaphthylamine” refers to the ring system:

The term “4-(phenylnaphthylamino)phenyl” refers to the ring system

The term “4-(diphenylamino)phenyl” refers to the ring system:

The term “o-phenylene” refers to:

The term “1,3 interphenylene” refers to the ring system:

The term “1,4 interphenylene” refers to the ring system:

The term “perfluoroalkyl” refers to fluoroalkyl with a formulaC_(n)F_(2n+1) for a linear or branched structure, wherein n is anyinteger, such as 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10, e.g., CF₃, C₂F₅,C₃F₇, C₄F₉, C₅F₁₁, C₆F₁₃, etc., or C_(n)F_(2n) for a cyclic structure,e.g., cyclic C₃F₆, cyclic C₄F₈, cyclic C₅F₁₀, cyclic C₆F₁₂, etc. Inother words, every hydrogen atom in alkyl is replaced by fluorine. Forexample, while not intending to be limiting, C₁₋₃ perfluoroalkyl refersto CF₃, C₂F₅, and C₃F₇ isomers. The term “perfluoroalkyl” refers tofluoroalkyl with a formula C_(n)F_(2n+1) for a linear or branchedstructure, e.g., CF₃, C₂F₅, C₃F₇, C₄F₉, C₅F₁₁, C₆F₁₃, etc., orC_(n)F_(2n) for a cyclic structure, e.g., cyclic C₃F₆, cyclic C₄F₈,cyclic C₅F₁₀, cyclic C₆F₁₂, etc. In other words, every hydrogen atom inalkyl is replaced by fluorine. For example, while not intending to belimiting, C₁₋₃ perfluoroalkyl refers to CF₃, C₂F₅, and C₃F₇ isomers.

With respect to Formula 1, Ph¹ is optionally substituted o-phenylene. Ifthe o-phenylene is substituted, it may have 1, 2, 3, or 4 substituents.Any substituent can be included on the o-phenylene. In some embodiments,some or all of the substituents on the o-phenylene may have: from 0 to15 carbon atoms and from 0 to 10 heteroatoms independently selectedfrom: O, N, S, F, Cl, Br, and I; and/or a molecular weight of 15 g/molto 500 g/mol. For example, the substituents may be C₁₋₁₀ alkyl, such asCH₃, C₂H₅, C₃H₇, cyclic C₃H₅, C₄H₉, cyclic C₄H₇, C₅H₁₁, cyclic C₅H₉,C₆H₁₃, cyclic C₆H₁₁, etc.; C₁₋₁₀ alkoxy; halo, such as F, Cl, Br, I; OH;CN; NO₂; C₁₋₆ fluoroalkyl, such as CF₃, CF₂H, C₂F₅, etc.; a C₁₋₁₀ estersuch as —O₂CCH₃, —CO₂CH₃, —O₂CC₂H₅, —CO₂C₂H₅, —O₂C-phenyl, —CO₂-phenyl,etc.; a C₁₋₁₀ ketone such as —COCH₃, —COC₂H₅, —COC₃H₇, —CO-phenyl, etc.;or a C₁₋₁₀ amine such as NH₂, NH(CH₃), N(CH₃)₂, N(CH₃)C₂H₅, etc. In someembodiments, any substituents of the o-phenylene are C₁₋₃ alkyl or C₁₋₃perfluoroalkyl.

With respect to Formula 1, in some embodiments Ph¹ is:

With respect to Formula 1, Ph² is optionally substituted o-phenylene. Ifthe o-phenylene is substituted, it may have 1, 2, 3, or 4 substituents.Any substituent can be included on the o-phenylene. In some embodiments,some or all of the substituents on the o-phenylene may have: from 0 to15 carbon atoms and from 0 to 10 heteroatoms independently selectedfrom: O, N, S, F, Cl, Br, and I; and/or a molecular weight of 15 g/molto 500 g/mol. For example, the substituents may be C₁₋₁₀ alkyl, such asCH₃, C₂H₅, C₃H₇, cyclic C₃H₅, C₄H₉, cyclic C₄H₇, C₅H₁₁, cyclic C₅H₉,C₆H₁₃, cyclic C₆H₁₁, etc.; C₁₋₁₀ alkoxy; halo, such as F, Cl, Br, I; OH;CN; NO₂; C₁₋₆ fluoroalkyl, such as CF₃, CF₂H, C₂F₅, etc.; a C₁₋₁₀ estersuch as —O₂CCH₃, —CO₂CH₃, —O₂CC₂H₅, —CO₂C₂H₅, —O₂C-phenyl, —CO₂-phenyl,etc.; a C₁₋₁₀ ketone such as —COCH₃, —COC₂H₅, —COC₃H₇, —CO-phenyl, etc.;or a C₁₋₁₀ amine such as NH₂, NH(CH₃), N(CH₃)₂, N(CH₃)C₂H₅, etc. In someembodiments, any substituents of the o-phenylene are C₁₋₃ alkyl or C₁₋₃perfluoroalkyl.

With respect to Formula 1, in some embodiments, Ph² is:

Some embodiments include a compound represented by Formula 2 or 3:

With respect to Formula 1, 2, or 3, HT is an optionally substitutedphenylcarbazolyl, optionally substituted (phenylcarbazolyl)phenyl,optionally substituted 4-(phenylnaphthylamino)phenyl, or optionallysubstituted 4-(diphenylamino)phenyl. If HT is optionally substitutedphenylcarbazolyl, it can have 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, or12 substituents. If HT is optionally substituted(phenylcarbazolyl)phenyl, it can have 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10,11, 12, 13, 14, 15, or 16 substituents. In some embodiments, HT isoptionally substituted 4-(phenylcarbazolyl)phenyl. If HT is optionallysubstituted 4-(phenylnaphthylamino)phenyl, it can have 0, 1, 2, 3, 4, 5,6, 7, 8, 9, 10, 11, 12, 13, 14, 15, or 16 substituents. If HT isoptionally substituted 4-(diphenylamino)phenyl, it can have 0, 1, 2, 3,4, 5, 6, 7, 8, 9, 10, 11, 12, 13, or 14 substituents. Any substituentcan be included on HT. In some embodiments, some or all of thesubstituents on HT may have: from 0 to 15 carbon atoms and from 0 to 10heteroatoms independently selected from: O, N, S, F, Cl, Br, and I;and/or a molecular weight of 15 g/mol to 500 g/mol. For example, thesubstituents may be C₁₋₁₀ alkyl, such as CH₃, C₂H₅, C₃H₇, cyclic C₃H₅,C₄H₉, cyclic C₄H₇, C₅H₁₁, cyclic C₅H₉, C₆H₁₃, cyclic C₆H₁₁, etc.; C₁₋₁₀alkoxy; halo, such as F, Cl, Br, I; OH; CN; NO₂; C₁₋₆ fluoroalkyl, suchas CF₃, CF₂H, C₂F₅, etc.; a C₁₋₁₀ ester such as —O₂CCH₃, —CO₂CH₃,—O₂CC₂H₅, —CO₂C₂H₅, —O₂C-phenyl, —CO₂-phenyl, etc.; a C₁₋₁₀ ketone suchas —COCH₃, —COC₂H₅, —COC₃H₇, —CO-phenyl, etc.; or a C₁₋₁₀ amine such asNH₂, NH(CH₃), N(CH₃)₂, N(CH₃)C₂H₅, etc. In some embodiments, HT haselectron withdrawing substituents, including any group that can withdrawelectron density from the parent ring system, such as NO₂, CN, C₁₋₆acyl, C₁₋₆ alkylcarboxylate, C₁₋₆ fluoroalkyl, F, Cl, etc. In someembodiments, any substituents of HT are C₁₋₃ alkyl or C₁₋₃perfluoroalkyl.

With respect to Formula 1, 2, or 3, in some embodiments HT is:

With respect to Formula 1, 2, or 3, in some embodiments HT is:

With respect to Formula 1, 2, or 3, in some embodiments HT is:

In another embodiment, HT can be:

With respect to Formula 1 or 2, ET is optionally substitutedbenzimidazol-2-yl, optionally substituted benzimidazol-2-ylphenyl,optionally substituted di(benzimidazol-2-yl)phenyl, optionallysubstituted benzothiazol-2-ylphenyl, optionally substitutedbenzoxazol-2-ylphenyl, optionally substituted di(benzoxazol-2-yl)phenyl,optionally substituted 3,3′-bipyridin-5-yl, optionally substitutedquinolin-8-yl, optionally substituted quinolin-5-yl, or optionallysubstituted quinoxalin-5-yl.

With respect to Formula 1 or 2, any substituent can be included on ET.In some embodiments, some or all of the substituents on ET may have:from 0 to 15 carbon atoms and from 0 to 10 heteroatoms independentlyselected from: O, N, S, F, Cl, Br, and I; and/or a molecular weight of15 g/mol to 500 g/mol. For example, the substituents may be C₁₋₁₀ alkyl,such as CH₃, C₂H₅, C₃H₇, cyclic C₃H₅, C₄H₉, cyclic C₄H₇, C₅H₁₁, cyclicC₅H₉, C₆H₁₃, cyclic C₆H₁₁, etc.; C₁₋₁₀ alkoxy; halo, such as F, Cl, Br,I; OH; CN; NO₂; C₁₋₆ fluoroalkyl, such as CF₃, CF₂H, C₂F₅, etc.; a C₁₋₁₀ester such as —O₂CCH₃, —CO₂CH₃, —O₂CC₂H₅, —CO₂C₂H₅, —O₂C-phenyl,—CO₂-phenyl, etc.; a C₁₋₁₀ ketone such as —COCH₃, —COC₂H₅, —COC₃H₇,—CO-phenyl, etc.; or a C₁₋₁₀ amine such as NH₂, NH(CH₃), N(CH₃)₂,N(CH₃)C₂H₅, etc. In some embodiments, ET has electron donatingsubstituents, including any group that can donate electron density tothe parent ring system, such as C₁₋₆ alkyl, C₁₋₆ alkoxy, a C₁₋₆ amine,etc. In some embodiments, any substituents of ET are C₁₋₃ alkyl or C₁₋₃perfluoroalkyl.

With respect to Formula 1 or 2, in some embodiments ET is:

With respect to Formula 1 or 2, in some embodiments ET is:

With respect to Formula 1 or 2, in some embodiments ET is:

With respect to any relevant structural representation, such as MoietyA, Moiety B, or Moiety C, Ph³ is phenylene, Het¹ is optionallysubstituted 1-phenylbenzimidazol-2-yl or optionally substitutedbenzoxazol-2-yl; and Het² is H, is optionally substituted1-phenylbenzimidazol-2-yl, or optionally substituted benzoxazol-2-yl.

If Het¹ is optionally substituted 1-phenylbenzimidazol-2-yl, it can have0, 1, 2, 3, 4, 5, 6, 7, 8, or 9 substituents. If Het¹ is optionallysubstituted benzoxazol-2-yl, it can have 0, 1, 2, 3, or 4 substituents.

In some embodiments, Het¹ is

In some embodiments, Het¹ is

In some embodiments, Het¹ is

If Het² is optionally substituted 1-phenylbenzimidazol-2-yl, it can have0, 1, 2, 3, 4, 5, 6, 7, 8, or 9 substituents. If Het² is optionallysubstituted benzoxazol-2-yl, it can have 0, 1, 2, 3, or 4 substituents.

In some embodiments, Het² is H.

In some embodiments, Het² is

In some embodiments, Het² is

In some embodiments, Het² is

With respect to Formula 1 or 2, in some embodiments ET is:

With respect to Formula 1 or 2, in some embodiments ET is:

With respect to Formula 1 or 2, in some embodiments ET is:

With respect to Formula 1 or 2, in some embodiments ET is:

With respect to Formula 1 or 2, in some embodiments ET is:

In another embodiment, ET can be:

With respect to Formula 3, ET² is an optionally substitutedbenzimidazol-2-yl.

With respect to any relevant structural representations, such asFormulas 2, 3, 4, 5, 6, 7, 8, or 9, R¹⁻⁶⁰ may be H or any substituent,such as a substituent having from 0 to 6 carbon atoms and from 0 to 5heteroatoms, wherein each heteroatom is independently: O, N, S, F, Cl,Br, or I, and/or having a molecular weight of 15 g/mol to 300 g/mol. Anyof R¹-R⁶⁰ may comprise: a) 1 or more alkyl moieties optionallysubstituted with, or optionally connected by or to, b) 1 or morefunctional groups, such as C═C, C≡C, CO, CO₂, CON, NCO₂, OH, SH, O, S,N, N═C, F, Cl, Br, I, CN, NO₂, CO₂H, NH₂, etc.; or may be a substituenthaving no alkyl portion, such as F, Cl, Br, I, NO₂, CN, NH₂, OH, COH,CO₂H, etc.

With respect to any relevant structural representations, such asFormulas 2, 3, 4, 5, 6, 7, 8, or 9, some non-limiting examples of R¹⁻⁶⁰may independently include R^(A), F, Cl, CN, OR^(A), CF₃, NO₂,NR^(A)R^(B), COR^(A), CO₂R^(A), OCORA, NR^(A)COR^(B), CONR^(A)R^(B),etc. In some embodiments, R¹⁻⁶⁰ may be may be H; F; Cl; CN; CF₃; OH;NH₂; C₁₋₆ alkyl, such as methyl, ethyl, propyl isomers (e.g. n-propyland isopropyl), cyclopropyl, butyl isomers, cyclobutyl isomers (e.g.cyclobutyl and methylcyclopropyl), pentyl isomers, cyclopentyl isomers,hexyl isomers, cyclohexyl isomers, etc.; C₁₋₆ amino, such as —NHCH₃,—NH(CH₃)₂, —NHCH₂CH₃, etc.; C₁₋₆ alkoxy, such as —O-methyl, —O-ethyl,isomers of —O-propyl, —O-cyclopropyl, isomers of —O-butyl, isomers of—O-cyclobutyl, isomers of —O-pentyl, isomers of —O-cyclopentyl, isomersof —O-hexyl, isomers of —O-cyclohexyl, etc.; CHO; C₂₋₆—CO-alkyl, such as—COCH₃, —COC₂H₅, —COC₃H₇, COC₄H₉, —COC₅H₁₁, etc.; CO₂H; C₂₋₆—CO₂-alkyl,—CO₂CH₃, —CO₂C₂H₅, —CO₂C₃H₇, CO₂C₄H₉, —COC₅H₁₁, etc. In someembodiments, R¹⁻⁶⁰ may independently be H, C₁-C₃ alkyl, or C₁₋₃perfluoroalkyl. In some embodiments, R¹⁻⁶⁰ may be H.

Each R^(A) may independently be H, or C₁₋₁₂ alkyl, including: linear orbranched alkyl having a formula C_(a)H_(a+1), or cycloalkyl having aformula C_(a)H_(a−1), wherein a is 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, or12, such as linear or branched alkyl of a formula: CH₃, C₂H₅, C₃H₇,C₄H₉, C₅H₁₁, C₆H₁₃, C₇H₁₅, C₈H₁₇, C₉H₁₉, C₁₀H₂₁, etc., or cycloalkyl ofa formula: C₃H₅, C₄H₇, C₅H₉, C₆H₁₁, C₇H₁₃, C₈H₁₅, C₉H₁₇, C₁₀H₁₉, etc. Insome embodiments, R^(A) may be H or C₁₋₆ alkyl. In some embodiments,R^(A) may be H or C₁₋₃ alkyl. In some embodiments, R^(A) may be H orCH₃. In some embodiments, R^(A) may be H.

Each R^(B) may independently be H, or C₁₋₁₂ alkyl, including: linear orbranched alkyl having a formula C_(a)H_(a+1), or cycloalkyl having aformula C_(a)H_(a), wherein a is 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, or12, such as linear or branched alkyl of a formula: CH₃, C₂H₅, C₃H₇,C₄H₉, C₅H₁₁, C₆H₁₃, C₈H₁₇, C₇H₁₅, C₉H₁₉, C₁₀H₂₁, etc., or cycloalkyl ofa formula: C₃H₅, C₄H₇, C₅H₉, C₆H₁₁, C₇H₁₃, C₈H₁₅, C₉H₁₇, C₁₀H₁₉, etc. Insome embodiments, R^(B) may be H or C₁₋₃ alkyl. In some embodiments,R^(B) may be H or CH₃. In some embodiments, R^(B) may be H.

With respect to any relevant structural representation, such as Formulas2, 3, 4, 5, 6, 7, 8, or 9, in some embodiments R¹ is H, C₁-C₃ alkyl, orC₁₋₃ perfluoroalkyl. In some embodiments, R¹ is H. Additionally, for anyembodiments recited in this paragraph, all remaining relevant groups ofR¹⁻⁶⁰ may independently be R^(A), F, Cl, CN, OR^(A), CF₃, NO₂,NR^(A)R^(B), COR^(A), CO₂R^(A), OCORA, NR^(A)COR^(B), CONR^(A)R^(B); mayindependently be H; F; Cl; CN; CF₃; OH; NH₂; C₁₋₆ alkyl; C₁₋₆ amino;C₁₋₆ alkoxy; CHO; C₂₋₆—CO-alkyl; CO₂H; or C₂₋₆—CO₂-alkyl; mayindependently be H, C₁-C₃ alkyl, or C₁₋₃ perfluoroalkyl; or may be H.

With respect to any relevant structural representation, such as Formulas2, 3, 4, 5, 6, 7, 8, or 9, in some embodiments R² is H, C₁-C₃ alkyl, orC₁₋₃ perfluoroalkyl. In some embodiments, R² is H. Additionally, for anyembodiments recited in this paragraph, all remaining relevant groups ofR¹⁻⁶⁰ may independently be R^(A), F, Cl, CN, OR^(A), CF₃, NO₂,NR^(A)R^(B), COR^(A), CO₂R^(A), OCORA, NR^(A)COR^(B), CONR^(A)R^(B); mayindependently be H; F; Cl; CN; CF₃; OH; NH₂; C₁₋₆ alkyl; C₁₋₆ amino;C₁₋₆ alkoxy; CHO; C₂₋₆—CO-alkyl; CO₂H; or C₂₋₆—CO₂-alkyl; mayindependently be H, C₁-C₃ alkyl, or C₁₋₃ perfluoroalkyl; or may be H.

With respect to any relevant structural representation, such as Formulas2, 3, 4, 5, 6, 7, 8, or 9, in some embodiments R³ is H, C₁-C₃ alkyl, orC₁₋₃ perfluoroalkyl. In some embodiments, R³ is H. Additionally, for anyembodiments recited in this paragraph, all remaining relevant groups ofR¹⁻⁶⁰ may independently be R^(A), F, Cl, CN, OR^(A), CF₃, NO₂,NR^(A)R^(B), COR^(A), CO₂R^(A), OCORA, NR^(A)COR^(B), CONR^(A)R^(B); mayindependently be H; F; Cl; CN; CF₃; OH; NH₂; C₁₋₆ alkyl; C₁₋₆ amino;C₁₋₆ alkoxy; CHO; C₂₋₆—CO-alkyl; CO₂H; or C₂₋₆—CO₂-alkyl; mayindependently be H, C₁-C₃ alkyl, or C₁₋₃ perfluoroalkyl; or may be H.

With respect to any relevant structural representation, such as Formulas2, 3, 4, 5, 6, 7, 8, or 9, in some embodiments R⁴ is H, C₁-C₃ alkyl, orC₁₋₃ perfluoroalkyl. In some embodiments, R⁴ is H. Additionally, for anyembodiments recited in this paragraph, all remaining relevant groups ofR¹⁻⁶⁰ may independently be R^(A), F, Cl, CN, OR^(A), CF₃, NO₂,NR^(A)R^(B), COR^(A), CO₂R^(A), OCORA, NR^(A)COR^(B), CONR^(A)R^(B); mayindependently be H; F; Cl; CN; CF₃; OH; NH₂; C₁₋₆ alkyl; C₁₋₆ amino;C₁₋₆ alkoxy; CHO; C₂₋₆—CO-alkyl; CO₂H; or C₂₋₆—CO₂-alkyl; mayindependently be H, C₁-C₃ alkyl, or C₁₋₃ perfluoroalkyl; or may be H.

With respect to any relevant structural representation, such as Formulas2, 3, 4, 5, 6, 7, 8, or 9, in some embodiments R⁵ is H, C₁-C₃ alkyl, orC₁₋₃ perfluoroalkyl. In some embodiments, R⁵ is H. Additionally, for anyembodiments recited in this paragraph, all remaining relevant groups ofR¹⁻⁶⁰ may independently be R^(A), F, Cl, CN, OR^(A), CF₃, NO₂,NR^(A)R^(B), COR^(A), CO₂R^(A), OCORA, NR^(A)COR^(B), CONR^(A)R^(B); mayindependently be H; F; Cl; CN; CF₃; OH; NH₂; C₁₋₆ alkyl; C₁₋₆ amino;C₁₋₆ alkoxy; CHO; C₂₋₆—CO-alkyl; CO₂H; or C₂₋₆—CO₂-alkyl; mayindependently be H, C₁-C₃ alkyl, or C₁₋₃ perfluoroalkyl; or may be H.

With respect to any relevant structural representation, such as Formulas2, 3, 4, 5, 6, 7, 8, or 9, in some embodiments R⁶ is H, C₁-C₃ alkyl, orC₁₋₃ perfluoroalkyl. In some embodiments, R⁶ is H. Additionally, for anyembodiments recited in this paragraph, all remaining relevant groups ofR¹⁻⁶⁰ may independently be R^(A), F, Cl, CN, OR^(A), CF₃, NO₂,NR^(A)R^(B), COR^(A), CO₂R^(A), OCORA, NR^(A)COR^(B), CONR^(A)R^(B); mayindependently be H; F; Cl; CN; CF₃; OH; NH₂; C₁₋₆ alkyl; C₁₋₆ amino;C₁₋₆ alkoxy; CHO; C₂₋₆—CO-alkyl; CO₂H; or C₂₋₆—CO₂-alkyl; mayindependently be H, C₁-C₃ alkyl, or C₁₋₃ perfluoroalkyl; or may be H.

With respect to any relevant structural representation, such as Formulas2, 3, 4, 5, 6, 7, 8, or 9, in some embodiments R⁷ is H, C₁-C₃ alkyl, orC₁₋₃ perfluoroalkyl. In some embodiments, R⁷ is H. Additionally, for anyembodiments recited in this paragraph, all remaining relevant groups ofR¹⁻⁶⁰ may independently be R^(A), F, Cl, CN, OR^(A), CF₃, NO₂,NR^(A)R^(B), COR^(A), CO₂R^(A), OCORA, NR^(A)COR^(B), CONR^(A)R^(B); mayindependently be H; F; Cl; CN; CF₃; OH; NH₂; C₁₋₆ alkyl; C₁₋₆ amino;C₁₋₆ alkoxy; CHO; C₂₋₆—CO-alkyl; CO₂H; or C₂₋₆—CO₂-alkyl; mayindependently be H, C₁-C₃ alkyl, or C₁₋₃ perfluoroalkyl; or may be H.

With respect to any relevant structural representation, such as Formulas2, 3, 4, 5, 6, 7, 8, or 9, in some embodiments R⁸ is H, C₁-C₃ alkyl, orC₁₋₃ perfluoroalkyl. In some embodiments, R⁸ is H. Additionally, for anyembodiments recited in this paragraph, all remaining relevant groups ofR¹⁻⁶⁰ may independently be R^(A), F, Cl, CN, OR^(A), CF₃, NO₂,NR^(A)R^(B), COR^(A), CO₂R^(A), OCORA, NR^(A)COR^(B), CONR^(A)R^(B); mayindependently be H; F; Cl; CN; CF₃; OH; NH₂; C₁₋₆ alkyl; C₁₋₆ amino;C₁₋₆ alkoxy; CHO; C₂₋₆—CO-alkyl; CO₂H; or C₂₋₆—CO₂-alkyl; mayindependently be H, C₁-C₃ alkyl, or C₁₋₃ perfluoroalkyl; or may be H.

With respect to any relevant structural representation, such as Formulas2, 3, 4, 5, 6, 7, 8, or 9, in some embodiments, R¹, R², R³, R⁴, R⁵, R⁶,R⁷ and R⁸ are H.

With respect to any relevant structural representation, such as Formulas3, 4, 5, 6, 7, 8, or 9, in some embodiments R⁹ is H, C₁-C₃ alkyl, orC₁₋₃ perfluoroalkyl. In some embodiments, R⁹ is H. Additionally, for anyembodiments recited in this paragraph, all remaining relevant groups ofR¹⁻⁶⁰ may independently be R^(A), F, Cl, CN, OR^(A), CF₃, NO₂,NR^(A)R^(B), COR^(A), CO₂R^(A), OCORA, NR^(A)COR^(B), CONR^(A)R^(B); mayindependently be H; F; Cl; CN; CF₃; OH; NH₂; C₁₋₆ alkyl; C₁₋₆ amino;C₁₋₆ alkoxy; CHO; C₂₋₆—CO-alkyl; CO₂H; or C₂₋₆—CO₂-alkyl; mayindependently be H, C₁-C₃ alkyl, or C₁₋₃ perfluoroalkyl; or may be H.

With respect to any relevant structural representation, such as Formulas3, 4, 5, 6, or 7, in some embodiments R¹⁰ is H, C₁-C₃ alkyl, or C₁₋₃perfluoroalkyl. In some embodiments, R¹⁰ is H. Additionally, for anyembodiments recited in this paragraph, all remaining relevant groups ofR¹⁻⁶⁰ may independently be R^(A), F, Cl, CN, OR^(A), CF₃, NO₂,NR^(A)R^(B), COR^(A), CO₂R^(A), OCORA, NR^(A)COR^(B), CONR^(A)R^(B); mayindependently be H; F; Cl; CN; CF₃; OH; NH₂; C₁₋₆ alkyl; C₁₋₆ amino;C₁₋₆ alkoxy; CHO; C₂₋₆—CO-alkyl; CO₂H; or C₂₋₆—CO₂-alkyl; mayindependently be H, C₁-C₃ alkyl, or C₁₋₃ perfluoroalkyl; or may be H.

With respect to any relevant structural representation, such as Formulas3, 4, 5, 6, or 7, in some embodiments R¹¹ is H, C₁-C₃ alkyl, or C₁₋₃perfluoroalkyl. In some embodiments, R¹¹ is H. Additionally, for anyembodiments recited in this paragraph, all remaining relevant groups ofR¹⁻⁶⁰ may independently be R^(A), F, Cl, CN, OR^(A), CF₃, NO₂,NR^(A)R^(B), COR^(A), CO₂R^(A), OCORA, NR^(A)COR^(B), CONR^(A)R^(B); mayindependently be H; F; Cl; CN; CF₃; OH; NH₂; C₁₋₆ alkyl; C₁₋₆ amino;C₁₋₆ alkoxy; CHO; C₂₋₆—CO-alkyl; CO₂H; or C₂₋₆—CO₂-alkyl; mayindependently be H, C₁-C₃ alkyl, or C₁₋₃ perfluoroalkyl; or may be H.

With respect to any relevant structural representation, such as Formulas3, 4, 5, 6, 7, 8, or 9, in some embodiments R¹² is H, C₁-C₃ alkyl, orC₁₋₃ perfluoroalkyl. In some embodiments, R¹² is H. Additionally, forany embodiments recited in this paragraph, all remaining relevant groupsof R¹⁻⁶⁰ may independently be R^(A), F, Cl, CN, OR^(A), CF₃, NO₂,NR^(A)R^(B), COR^(A), CO₂R^(A), OCORA, NR^(A)COR^(B), CONR^(A)R^(B); mayindependently be H; F; Cl; CN; CF₃; OH; NH₂; C₁₋₆ alkyl; C₁₋₆ amino;C₁₋₆ alkoxy; CHO; C₂₋₆—CO-alkyl; CO₂H; or C₂₋₆—CO₂-alkyl; mayindependently be H, C₁-C₃ alkyl, or C₁₋₃ perfluoroalkyl; or may be H.

With respect to any relevant structural representation, such as Formulas3, 4, 5, 6, 7, 8, or 9, in some embodiments R¹, R², R³, R⁴, R⁵, R⁶, R⁷,R⁸, R⁹, R¹⁹, R¹¹ and R¹² are independently H, C₁-C₃ alkyl, or C₁₋₃perfluoroalkyl. In some embodiments, R¹, R², R³, R⁴, R⁵, R⁶, R⁷, R⁸, R⁹,R¹⁹, R¹¹ and R¹² are H.

With respect to any relevant structural representation, such as Formulas4 or 6, in some embodiments R¹³ is H, C₁-C₃ alkyl, or C₁₋₃perfluoroalkyl. In some embodiments, R¹³ is H. Additionally, for anyembodiments recited in this paragraph, all remaining relevant groups ofR¹⁻⁶⁰ may independently be R^(A), F, Cl, CN, OR^(A), CF₃, NO₂,NR^(A)R^(B), COR^(A), CO₂R^(A), OCORA, NR^(A)COR^(B), CONR^(A)R^(B); mayindependently be H; F; Cl; CN; CF₃; OH; NH₂; C₁₋₆ alkyl; C₁₋₆ amino;C₁₋₆ alkoxy; CHO; C₂₋₆—CO-alkyl; CO₂H; or C₂₋₆—CO₂-alkyl; mayindependently be H, C₁-C₃ alkyl, or C₁₋₃ perfluoroalkyl; or may be H.

With respect to any relevant structural representation, such as Formulas4 or 6, in some embodiments R¹⁴ is H, C₁-C₃ alkyl, or C₁₋₃perfluoroalkyl. In some embodiments, R¹⁴ is H. Additionally, for anyembodiments recited in this paragraph, all remaining relevant groups ofR¹⁻⁶⁰ may independently be R^(A), F, Cl, CN, OR^(A), CF₃, NO₂,NR^(A)R^(B), COR^(A), CO₂R^(A), OCORA, NR^(A)COR^(B), CONR^(A)R^(B); mayindependently be H; F; Cl; CN; CF₃; OH; NH₂; C₁₋₆ alkyl; C₁₋₆ amino;C₁₋₆ alkoxy; CHO; C₂₋₆—CO-alkyl; CO₂H; or C₂₋₆—CO₂-alkyl; mayindependently be H, C₁-C₃ alkyl, or C₁₋₃ perfluoroalkyl; or may be H.

With respect to any relevant structural representation, such as Formulas4 or 6, in some embodiments R¹⁵ is H, C₁-C₃ alkyl, or C₁₋₃perfluoroalkyl. In some embodiments, R¹⁵ is H. Additionally, for anyembodiments recited in this paragraph, all remaining relevant groups ofR¹⁻⁶⁰ may independently be R^(A), F, Cl, CN, OR^(A), CF₃, NO₂,NR^(A)R^(B), COR^(A), CO₂R^(A), OCORA, NR^(A)COR^(B), CONR^(A)R^(B); mayindependently be H; F; Cl; CN; CF₃; OH; NH₂; C₁₋₆ alkyl; C₁₋₆ amino;C₁₋₆ alkoxy; CHO; C₂₋₆—CO-alkyl; CO₂H; or C₂₋₆—CO₂-alkyl; mayindependently be H, C₁-C₃ alkyl, or C₁₋₃ perfluoroalkyl; or may be H.

With respect to any relevant structural representation, such as Formulas4 or 6, in some embodiments R¹⁶ is H, C₁-C₃ alkyl, or C₁₋₃perfluoroalkyl. In some embodiments, R¹⁶ is H. Additionally, for anyembodiments recited in this paragraph, all remaining relevant groups ofR¹⁻⁶⁰ may independently be R^(A), F, Cl, CN, OR^(A), CF₃, NO₂,NR^(A)R^(B), COR^(A), CO₂R^(A), OCORA, NR^(A)COR^(B), CONR^(A)R^(B); mayindependently be H; F; Cl; CN; CF₃; OH; NH₂; C₁₋₆ alkyl; C₁₋₆ amino;C₁₋₆ alkoxy; CHO; C₂₋₆—CO-alkyl; CO₂H; or C₂₋₆—CO₂-alkyl; mayindependently be H, C₁-C₃ alkyl, or C₁₋₃ perfluoroalkyl; or may be H.

With respect to any relevant structural representation, such as Formulas5, 6, 7, 8, or 9, in some embodiments R¹⁷ is H, C₁-C₃ alkyl, or C₁₋₃perfluoroalkyl. In some embodiments, R¹⁷ is H. Additionally, for anyembodiments recited in this paragraph, all remaining relevant groups ofR¹⁻⁶⁰ may independently be R^(A), F, Cl, CN, OR^(A), CF₃, NO₂,NR^(A)R^(B), COR^(A), CO₂R^(A), OCORA, NR^(A)COR^(B), CONR^(A)R^(B); mayindependently be H; F; Cl; CN; CF₃; OH; NH₂; C₁₋₆ alkyl; C₁₋₆ amino;C₁₋₆ alkoxy; CHO; C₂₋₆—CO-alkyl; CO₂H; or C₂₋₆—CO₂-alkyl; mayindependently be H, C₁-C₃ alkyl, or C₁₋₃ perfluoroalkyl; or may be H.

With respect to any relevant structural representation, such as Formulas5, 6, 7, 8, or 9, in some embodiments R¹⁸ is H, C₁-C₃ alkyl, or C₁₋₃perfluoroalkyl. In some embodiments, R¹⁸ is H. Additionally, for anyembodiments recited in this paragraph, all remaining relevant groups ofR¹⁻⁶⁰ may independently be R^(A), F, Cl, CN, OR^(A), CF₃, NO₂,NR^(A)R^(B), COR^(A), CO₂R^(A), OCORA, NR^(A)COR^(B), CONR^(A)R^(B); mayindependently be H; F; Cl; CN; CF₃; OH; NH₂; C₁₋₆ alkyl; C₁₋₆ amino;C₁₋₆ alkoxy; CHO; C₂₋₆—CO-alkyl; CO₂H; or C₂₋₆—CO₂-alkyl; mayindependently be H, C₁-C₃ alkyl, or C₁₋₃ perfluoroalkyl; or may be H.

With respect to any relevant structural representation, such as Formulas5, 6, 7, 8, or 9, in some embodiments R¹⁹ is H, C₁-C₃ alkyl, or C₁₋₃perfluoroalkyl. In some embodiments, R¹⁹ is H. Additionally, for anyembodiments recited in this paragraph, all remaining relevant groups ofR¹⁻⁶⁰ may independently be R^(A), F, Cl, CN, OR^(A), CF₃, NO₂,NR^(A)R^(B), COR^(A), CO₂R^(A), OCORA, NR^(A)COR^(B), CONR^(A)R^(B); mayindependently be H; F; Cl; CN; CF₃; OH; NH₂; C₁₋₆ alkyl; C₁₋₆ amino;C₁₋₆ alkoxy; CHO; C₂₋₆—CO-alkyl; CO₂H; or C₂₋₆—CO₂-alkyl; mayindependently be H, C₁-C₃ alkyl, or C₁₋₃ perfluoroalkyl; or may be H.

With respect to any relevant structural representation, such as Formulas4, 6, 7, 8, or 9, in some embodiments R²¹ is H, C₁-C₃ alkyl, or C₁₋₃perfluoroalkyl. In some embodiments, R²¹ is H. Additionally, for anyembodiments recited in this paragraph, all remaining relevant groups ofR¹⁻⁶⁰ may independently be R^(A), F, Cl, CN, OR^(A), CF₃, NO₂,NR^(A)R^(B), COR^(A), CO₂R^(A), OCORA, NR^(A)COR^(B), CONR^(A)R^(B); mayindependently be H; F; Cl; CN; CF₃; OH; NH₂; C₁₋₆ alkyl; C₁₋₆ amino;C₁₋₆ alkoxy; CHO; C₂₋₆—CO-alkyl; CO₂H; or C₂₋₆—CO₂-alkyl; mayindependently be H, C₁-C₃ alkyl, or C₁₋₃ perfluoroalkyl; or may be H.

With respect to any relevant structural representation, such as Formulas4, 6, 7, 8, or 9, in some embodiments R²² is H, C₁-C₃ alkyl, or C₁₋₃perfluoroalkyl. In some embodiments, R²² is H. Additionally, for anyembodiments recited in this paragraph, all remaining relevant groups ofR¹⁻⁶⁰ may independently be R^(A), F, Cl, CN, OR^(A), CF₃, NO₂,NR^(A)R^(B), COR^(A), CO₂R^(A), OCORA, NR^(A)COR^(B), CONR^(A)R^(B); mayindependently be H; F; Cl; CN; CF₃; OH; NH₂; C₁₋₆ alkyl; C₁₋₆ amino;C₁₋₆ alkoxy; CHO; C₂₋₆—CO-alkyl; CO₂H; or C₂₋₆—CO₂-alkyl; mayindependently be H, C₁-C₃ alkyl, or C₁₋₃ perfluoroalkyl; or may be H.

With respect to any relevant structural representation, such as Formulas4, 6, 7, 8, or 9, in some embodiments R²³ is H, C₁-C₃ alkyl, or C₁₋₃perfluoroalkyl. In some embodiments, R²³ is H. Additionally, for anyembodiments recited in this paragraph, all remaining relevant groups ofR¹⁻⁶⁰ may independently be R^(A), F, Cl, CN, OR^(A), CF₃, NO₂,NR^(A)R^(B), COR^(A), CO₂R^(A), OCORA, NR^(A)COR^(B), CONR^(A)R^(B); mayindependently be H; F; Cl; CN; CF₃; OH; NH₂; C₁₋₆ alkyl; C₁₋₆ amino;C₁₋₆ alkoxy; CHO; C₂₋₆—CO-alkyl; CO₂H; or C₂₋₆—CO₂-alkyl; mayindependently be H, C₁-C₃ alkyl, or C₁₋₃ perfluoroalkyl; or may be H.

With respect to any relevant structural representation, such as Formulas4, 6, 7, 8, or 9, in some embodiments R²⁴ is H, C₁-C₃ alkyl, or C₁₋₃perfluoroalkyl. In some embodiments, R²⁴ is H. Additionally, for anyembodiments recited in this paragraph, all remaining relevant groups ofR¹⁻⁶⁰ may independently be R^(A), F, Cl, CN, OR^(A), CF₃, NO₂,NR^(A)R^(B), COR^(A), CO₂R^(A), OCORA, NR^(A)COR^(B), CONR^(A)R^(B); mayindependently be H; F; Cl; CN; CF₃; OH; NH₂; C₁₋₆ alkyl; C₁₋₆ amino;C₁₋₆ alkoxy; CHO; C₂₋₆—CO-alkyl; CO₂H; or C₂₋₆—CO₂-alkyl; mayindependently be H, C₁-C₃ alkyl, or C₁₋₃ perfluoroalkyl; or may be H.

With respect to any relevant structural representation, such as Formulas4, 6, 7, or 9, in some embodiments R²⁵ is H, C₁-C₃ alkyl, or C₁₋₃perfluoroalkyl. In some embodiments, R²⁵ is H. Additionally, for anyembodiments recited in this paragraph, all remaining relevant groups ofR¹⁻⁶⁰ may independently be R^(A), F, Cl, CN, OR^(A), CF₃, NO₂,NR^(A)R^(B), COR^(A), CO₂R^(A), OCORA, NR^(A)COR^(B), CONR^(A)R^(B); mayindependently be H; F; Cl; CN; CF₃; OH; NH₂; C₁₋₆ alkyl; C₁₋₆ amino;C₁₋₆ alkoxy; CHO; C₂₋₆—CO-alkyl; CO₂H; or C₂₋₆—CO₂-alkyl; mayindependently be H, C₁-C₃ alkyl, or C₁₋₃ perfluoroalkyl; or may be H.

With respect to any relevant structural representation, such as Formulas4, 6, 7, or 9, in some embodiments R²⁶ is H, C₁-C₃ alkyl, or C₁₋₃perfluoroalkyl. In some embodiments, R²⁶ is H. Additionally, for anyembodiments recited in this paragraph, all remaining relevant groups ofR¹⁻⁶⁰ may independently be R^(A), F, Cl, CN, OR^(A), CF₃, NO₂,NR^(A)R^(B), COR^(A), CO₂R^(A), OCORA, NR^(A)COR^(B), CONR^(A)R^(B); mayindependently be H; F; Cl; CN; CF₃; OH; NH₂; C₁₋₆ alkyl; C₁₋₆ amino;C₁₋₆ alkoxy; CHO; C₂₋₆—CO-alkyl; CO₂H; or C₂₋₆—CO₂-alkyl; mayindependently be H, C₁-C₃ alkyl, or C₁₋₃ perfluoroalkyl; or may be H.

With respect to any relevant structural representation, such as Formulas4, 6, 7, or 9, in some embodiments R²⁷ is H, C₁-C₃ alkyl, or C₁₋₃perfluoroalkyl. In some embodiments, R²⁷ is H. Additionally, for anyembodiments recited in this paragraph, all remaining relevant groups ofR¹⁻⁶⁰ may independently be R^(A), F, Cl, CN, OR^(A), CF₃, NO₂,NR^(A)R^(B), COR^(A), CO₂R^(A), OCORA, NR^(A)COR^(B), CONR^(A)R^(B); mayindependently be H; F; Cl; CN; CF₃; OH; NH₂; C₁₋₆ alkyl; C₁₋₆ amino;C₁₋₆ alkoxy; CHO; C₂₋₆—CO-alkyl; CO₂H; or C₂₋₆—CO₂-alkyl; mayindependently be H, C₁-C₃ alkyl, or C₁₋₃ perfluoroalkyl; or may be H.

With respect to any relevant structural representation, such as Formulas4, 6, 7, or 9, in some embodiments R²⁸ is H, C₁-C₃ alkyl, or C₁₋₃perfluoroalkyl. In some embodiments, R²⁸ is H. Additionally, for anyembodiments recited in this paragraph, all remaining relevant groups ofR¹⁻⁶⁰ may independently be R^(A), F, Cl, CN, OR^(A), CF₃, NO₂,NR^(A)R^(B), COR^(A), CO₂R^(A), OCORA, NR^(A)COR^(B), CONR^(A)R^(B); mayindependently be H; F; Cl; CN; CF₃; OH; NH₂; C₁₋₆ alkyl; C₁₋₆ amino;C₁₋₆ alkoxy; CHO; C₂₋₆—CO-alkyl; CO₂H; or C₂₋₆—CO₂-alkyl; mayindependently be H, C₁-C₃ alkyl, or C₁₋₃ perfluoroalkyl; or may be H.

With respect to any relevant structural representation, such as Formulas4, 6, 7, or 9, in some embodiments R²⁹ is H, C₁-C₃ alkyl, or C₁₋₃perfluoroalkyl. In some embodiments, R²⁹ is H. Additionally, for anyembodiments recited in this paragraph, all remaining relevant groups ofR¹⁻⁶⁰ may independently be R^(A), F, Cl, CN, OR^(A), CF₃, NO₂,NR^(A)R^(B), COR^(A), CO₂R^(A), OCORA, NR^(A)COR^(B), CONR^(A)R^(B); mayindependently be H; F; Cl; CN; CF₃; OH; NH₂; C₁₋₆ alkyl; C₁₋₆ amino;C₁₋₆ alkoxy; CHO; C₂₋₆—CO-alkyl; CO₂H; or C₂₋₆—CO₂-alkyl; mayindependently be H, C₁-C₃ alkyl, or C₁₋₃ perfluoroalkyl; or may be H.

With respect to any relevant structural representation, such as Formula4, in some embodiments R³⁰ is H, C₁-C₃ alkyl, or C₁₋₃ perfluoroalkyl. Insome embodiments, R³⁰ is H. Additionally, for any embodiments recited inthis paragraph, all remaining relevant groups of R¹⁻⁶⁰ may independentlybe R^(A), F, Cl, CN, OR^(A), CF₃, NO₂, NR^(A)R^(B), COR^(A), CO₂R^(A),OCORA, NR^(A)COR^(B), CONR^(A)R^(B); may independently be H; F; Cl; CN;CF₃; OH; NH₂; C₁₋₆ alkyl; C₁₋₆ amino; C₁₋₆ alkoxy; CHO; C₂₋₆—CO-alkyl;CO₂H; or C₂₋₆—CO₂-alkyl; may independently be H, C₁-C₃ alkyl, or C₁₋₃perfluoroalkyl; or may be H.

With respect to any relevant structural representation, such as Formula4, in some embodiments R³¹ is H, C₁-C₃ alkyl, or C₁₋₃ perfluoroalkyl. Insome embodiments, R³¹ is H. Additionally, for any embodiments recited inthis paragraph, all remaining relevant groups of R¹⁻⁶⁰ may independentlybe R^(A), F, Cl, CN, OR^(A), CF₃, NO₂, NR^(A)R^(B), COR^(A), CO₂R^(A),OCORA, NR^(A)COR^(B), CONR^(A)R^(B); may independently be H; F; Cl; CN;CF₃; OH; NH₂; C₁₋₆ alkyl; C₁₋₆ amino; C₁₋₆ alkoxy; CHO; C₂₋₆—CO-alkyl;CO₂H; or C₂₋₆—CO₂-alkyl; may independently be H, C₁-C₃ alkyl, or C₁₋₃perfluoroalkyl; or may be H.

With respect to any relevant structural representation, such as Formula4, in some embodiments R³² is H, C₁-C₃ alkyl, or C₁₋₃ perfluoroalkyl. Insome embodiments, R³² is H. Additionally, for any embodiments recited inthis paragraph, all remaining relevant groups of R¹⁻⁶⁰ may independentlybe R^(A), F, Cl, CN, OR^(A), CF₃, NO₂, NR^(A)R^(B), COR^(A), CO₂R^(A),OCORA, NR^(A)COR^(B), CONR^(A)R^(B); may independently be H; F; Cl; CN;CF₃; OH; NH₂; C₁₋₆ alkyl; C₁₋₆ amino; C₁₋₆ alkoxy; CHO; C₂₋₆—CO-alkyl;CO₂H; or C₂₋₆—CO₂-alkyl; may independently be H, C₁-C₃ alkyl, or C₁₋₃perfluoroalkyl; or may be H.

With respect to any relevant structural representation, such as Formula4, in some embodiments R³³ is H, C₁-C₃ alkyl, or C₁₋₃ perfluoroalkyl. Insome embodiments, R³³ is H. Additionally, for any embodiments recited inthis paragraph, all remaining relevant groups of R¹⁻⁶⁰ may independentlybe R^(A), F, Cl, CN, OR^(A), CF₃, NO₂, NR^(A)R^(B), COR^(A), CO₂R^(A),OCORA, NR^(A)COR^(B), CONR^(A)R^(B); may independently be H; F; Cl; CN;CF₃; OH; NH₂; C₁₋₆ alkyl; C₁₋₆ amino; C₁₋₆ alkoxy; CHO; C₂₋₆—CO-alkyl;CO₂H; or C₂₋₆—CO₂-alkyl; may independently be H, C₁-C₃ alkyl, or C₁₋₃perfluoroalkyl; or may be H.

With respect to any relevant structural representation, such as Formula4, in some embodiments R³⁴ is H, C₁-C₃ alkyl, or C₁₋₃ perfluoroalkyl. Insome embodiments, R³⁴ is H. Additionally, for any embodiments recited inthis paragraph, all remaining relevant groups of R¹⁻⁶⁰ may independentlybe R^(A), F, Cl, CN, OR^(A), CF₃, NO₂, NR^(A)R^(B), COR^(A), CO₂R^(A),OCORA, NR^(A)COR^(B), CONR^(A)R^(B); may independently be H; F; Cl; CN;CF₃; OH; NH₂; C₁₋₆ alkyl; C₁₋₆ amino; C₁₋₆ alkoxy; CHO; C₂₋₆—CO-alkyl;CO₂H; or C₂₋₆—CO₂-alkyl; may independently be H, C₁-C₃ alkyl, or C₁₋₃perfluoroalkyl; or may be H.

With respect to any relevant structural representation, such as Formula4, in some embodiments R³⁵ is H, C₁-C₃ alkyl, or C₁₋₃ perfluoroalkyl. Insome embodiments, R³⁵ is H. Additionally, for any embodiments recited inthis paragraph, all remaining relevant groups of R¹⁻⁶⁰ may independentlybe R^(A), F, Cl, CN, OR^(A), CF₃, NO₂, NR^(A)R^(B), COR^(A), CO₂R^(A),OCORA, NR^(A)COR^(B), CONR^(A)R^(B); may independently be H; F; Cl; CN;CF₃; OH; NH₂; C₁₋₆ alkyl; C₁₋₆ amino; C₁₋₆ alkoxy; CHO; C₂₋₆—CO-alkyl;CO₂H; or C₂₋₆—CO₂-alkyl; may independently be H, C₁-C₃ alkyl, or C₁₋₃perfluoroalkyl; or may be H.

With respect to any relevant structural representation, such as Formula4, in some embodiments R³⁶ is H, C₁-C₃ alkyl, or C₁₋₃ perfluoroalkyl. Insome embodiments, R³⁶ is H. Additionally, for any embodiments recited inthis paragraph, all remaining relevant groups of R¹⁻⁶⁰ may independentlybe R^(A), F, Cl, CN, OR^(A), CF₃, NO₂, NR^(A)R^(B), COR^(A), CO₂R^(A),OCORA, NR^(A)COR^(B), CONR^(A)R^(B); may independently be H; F; Cl; CN;CF₃; OH; NH₂; C₁₋₆ alkyl; C₁₋₆ amino; C₁₋₆ alkoxy; CHO; C₂₋₆—CO-alkyl;CO₂H; or C₂₋₆—CO₂-alkyl; may independently be H, C₁-C₃ alkyl, or C₁₋₃perfluoroalkyl; or may be H.

With respect to any relevant structural representation, such as Formula4, in some embodiments R³⁷ is H, C₁-C₃ alkyl, or C₁₋₃ perfluoroalkyl. Insome embodiments, R³⁷ is H. Additionally, for any embodiments recited inthis paragraph, all remaining relevant groups of R¹⁻⁶⁰ may independentlybe R^(A), F, Cl, CN, OR^(A), CF₃, NO₂, NR^(A)R^(B), COR^(A), CO₂R^(A),OCORA, NR^(A)COR^(B), CONR^(A)R^(B); may independently be H; F; Cl; CN;CF₃; OH; NH₂; C₁₋₆ alkyl; C₁₋₆ amino; C₁₋₆ alkoxy; CHO; C₂₋₆—CO-alkyl;CO₂H; or C₂₋₆—CO₂-alkyl; may independently be H, C₁-C₃ alkyl, or C₁₋₃perfluoroalkyl; or may be H.

With respect to any relevant structural representation, such as Formula4, in some embodiments R³⁸ is H, C₁-C₃ alkyl, or C₁₋₃ perfluoroalkyl. Insome embodiments, R³⁸ is H. Additionally, for any embodiments recited inthis paragraph, all remaining relevant groups of R¹⁻⁶⁰ may independentlybe R^(A), F, Cl, CN, OR^(A), CF₃, NO₂, NR^(A)R^(B), COR^(A), CO₂R^(A),OCORA, NR^(A)COR^(B), CONR^(A)R^(B); may independently be H; F; Cl; CN;CF₃; OH; NH₂; C₁₋₆ alkyl; C₁₋₆ amino; C₁₋₆ alkoxy; CHO; C₂₋₆—CO-alkyl;CO₂H; or C₂₋₆—CO₂-alkyl; may independently be H, C₁-C₃ alkyl, or C₁₋₃perfluoroalkyl; or may be H.

With respect to any relevant structural representation, such as Formula4, in some embodiments R³⁹ is H, C₁-C₃ alkyl, or C₁₋₃ perfluoroalkyl. Insome embodiments, R³⁹ is H. Additionally, for any embodiments recited inthis paragraph, all remaining relevant groups of R¹⁻⁶⁰ may independentlybe R^(A), F, Cl, CN, OR^(A), CF₃, NO₂, NR^(A)R^(B), COR^(A), CO₂R^(A),OCORA, NR^(A)COR^(B), CONR^(A)R^(B); may independently be H; F; Cl; CN;CF₃; OH; NH₂; C₁₋₆ alkyl; C₁₋₆ amino; C₁₋₆ alkoxy; CHO; C₂₋₆—CO-alkyl;CO₂H; or C₂₋₆—CO₂-alkyl; may independently be H, C₁-C₃ alkyl, or C₁₋₃perfluoroalkyl; or may be H.

With respect to any relevant structural representation, such as Formula4, in some embodiments R⁴⁰ is H, C₁-C₃ alkyl, or C₁₋₃ perfluoroalkyl. Insome embodiments, R⁴⁰ is H. Additionally, for any embodiments recited inthis paragraph, all remaining relevant groups of R¹⁻⁶⁰ may independentlybe R^(A), F, Cl, CN, OR^(A), CF₃, NO₂, NR^(A)R^(B), COR^(A), CO₂R^(A),OCORA, NR^(A)COR^(B), CONR^(A)R^(B); may independently be H; F; Cl; CN;CF₃; OH; NH₂; C₁₋₆ alkyl; C₁₋₆ amino; C₁₋₆ alkoxy; CHO; C₂₋₆—CO-alkyl;CO₂H; or C₂₋₆—CO₂-alkyl; may independently be H, C₁-C₃ alkyl, or C₁₋₃perfluoroalkyl; or may be H.

With respect to any relevant structural representation, such as Formula4, in some embodiments R⁴¹ is H, C₁-C₃ alkyl, or C₁₋₃ perfluoroalkyl. Insome embodiments, R⁴¹ is H. Additionally, for any embodiments recited inthis paragraph, all remaining relevant groups of R¹⁻⁶⁰ may independentlybe R^(A), F, Cl, CN, OR^(A), CF₃, NO₂, NR^(A)R^(B), COR^(A), CO₂R^(A),OCORA, NR^(A)COR^(B), CONR^(A)R^(B); may independently be H; F; Cl; CN;CF₃; OH; NH₂; C₁₋₆ alkyl; C₁₋₆ amino; C₁₋₆ alkoxy; CHO; C₂₋₆—CO-alkyl;CO₂H; or C₂₋₆—CO₂-alkyl; may independently be H, C₁-C₃ alkyl, or C₁₋₃perfluoroalkyl; or may be H.

With respect to any relevant structural representation, such as Formulas5, 6, 7, 8, or 9, in some embodiments R⁴² is H, C₁-C₃ alkyl, or C₁₋₃perfluoroalkyl. In some embodiments, R⁴² is H. Additionally, for anyembodiments recited in this paragraph, all remaining relevant groups ofR¹⁻⁶⁰ may independently be R^(A), F, Cl, CN, OR^(A), CF₃, NO₂,NR^(A)R^(B), COR^(A), CO₂R^(A), OCORA, NR^(A)COR^(B), CONR^(A)R^(B); mayindependently be H; F; Cl; CN; CF₃; OH; NH₂; C₁₋₆ alkyl; C₁₋₆ amino;C₁₋₆ alkoxy; CHO; C₂₋₆—CO-alkyl; CO₂H; or C₂₋₆—CO₂-alkyl; mayindependently be H, C₁-C₃ alkyl, or C₁₋₃ perfluoroalkyl; or may be H.

With respect to any relevant structural representation, such as Formulas5, 6, 7, 8, or 9, in some embodiments R⁴³ is H, C₁-C₃ alkyl, or C₁₋₃perfluoroalkyl. In some embodiments, R⁴³ is H. Additionally, for anyembodiments recited in this paragraph, all remaining relevant groups ofR¹⁻⁶⁰ may independently be R^(A), F, Cl, CN, OR^(A), CF₃, NO₂,NR^(A)R^(B), COR^(A), CO₂R^(A), OCORA, NR^(A)COR^(B), CONR^(A)R^(B); mayindependently be H; F; Cl; CN; CF₃; OH; NH₂; C₁₋₆ alkyl; C₁₋₆ amino;C₁₋₆ alkoxy; CHO; C₂₋₆—CO-alkyl; CO₂H; or C₂₋₆—CO₂-alkyl; mayindependently be H, C₁-C₃ alkyl, or C₁₋₃ perfluoroalkyl; or may be H.

With respect to any relevant structural representation, such as Formulas5, 6, 7, 8, or 9, in some embodiments R⁴⁴ is H, C₁-C₃ alkyl, or C₁₋₃perfluoroalkyl. In some embodiments, R⁴⁴ is H. Additionally, for anyembodiments recited in this paragraph, all remaining relevant groups ofR¹⁻⁶⁰ may independently be R^(A), F, Cl, CN, OR^(A), CF₃, NO₂,NR^(A)R^(B), COR^(A), CO₂R^(A), OCORA, NR^(A)COR^(B), CONR^(A)R^(B); mayindependently be H; F; Cl; CN; CF₃; OH; NH₂; C₁₋₆ alkyl; C₁₋₆ amino;C₁₋₆ alkoxy; CHO; C₂₋₆—CO-alkyl; CO₂H; or C₂₋₆—CO₂-alkyl; mayindependently be H, C₁-C₃ alkyl, or C₁₋₃ perfluoroalkyl; or may be H.

With respect to any relevant structural representation, such as Formulas5, 6, 7, 8, or 9, in some embodiments R⁴⁵ is H, C₁-C₃ alkyl, or C₁₋₃perfluoroalkyl. In some embodiments, R⁴⁵ is H. Additionally, for anyembodiments recited in this paragraph, all remaining relevant groups ofR¹⁻⁶⁰ may independently be R^(A), F, Cl, CN, OR^(A), CF₃, NO₂,NR^(A)R^(B), COR^(A), CO₂R^(A), OCORA, NR^(A)COR^(B), CONR^(A)R^(B); mayindependently be H; F; Cl; CN; CF₃; OH; NH₂; C₁₋₆ alkyl; C₁₋₆ amino;C₁₋₆ alkoxy; CHO; C₂₋₆—CO-alkyl; CO₂H; or C₂₋₆—CO₂-alkyl; mayindependently be H, C₁-C₃ alkyl, or C₁₋₃ perfluoroalkyl; or may be H.

With respect to any relevant structural representation, such as Formulas5, 6, 7, 8, or 9, in some embodiments R⁴⁶ is H, C₁-C₃ alkyl, or C₁₋₃perfluoroalkyl. In some embodiments, R⁴⁶ is H. Additionally, for anyembodiments recited in this paragraph, all remaining relevant groups ofR¹⁻⁶⁰ may independently be R^(A), F, Cl, CN, OR^(A), CF₃, NO₂,NR^(A)R^(B), COR^(A), CO₂R^(A), OCORA, NR^(A)COR^(B), CONR^(A)R^(B); mayindependently be H; F; Cl; CN; CF₃; OH; NH₂; C₁₋₆ alkyl; C₁₋₆ amino;C₁₋₆ alkoxy; CHO; C₂₋₆—CO-alkyl; CO₂H; or C₂₋₆—CO₂-alkyl; mayindependently be H, C₁-C₃ alkyl, or C₁₋₃ perfluoroalkyl; or may be H.

With respect to any relevant structural representation, such as Formulas5, 6, 7, 8, or 9, in some embodiments R⁴⁷ is H, C₁-C₃ alkyl, or C₁₋₃perfluoroalkyl. In some embodiments, R⁴⁷ is H. Additionally, for anyembodiments recited in this paragraph, all remaining relevant groups ofR¹⁻⁶⁰ may independently be R^(A), F, Cl, CN, OR^(A), CF₃, NO₂,NR^(A)R^(B), COR^(A), CO₂R^(A), OCORA, NR^(A)COR^(B), CONR^(A)R^(B); mayindependently be H; F; Cl; CN; CF₃; OH; NH₂; C₁₋₆ alkyl; C₁₋₆ amino;C₁₋₆ alkoxy; CHO; C₂₋₆—CO-alkyl; CO₂H; or C₂₋₆—CO₂-alkyl; mayindependently be H, C₁-C₃ alkyl, or C₁₋₃ perfluoroalkyl; or may be H.

With respect to any relevant structural representation, such as Formulas5, 6, 7, 8, or 9, in some embodiments R⁴⁸ is H, C₁-C₃ alkyl, or C₁₋₃perfluoroalkyl. In some embodiments, R⁴⁸ is H. Additionally, for anyembodiments recited in this paragraph, all remaining relevant groups ofR¹⁻⁶⁰ may independently be R^(A), F, Cl, CN, OR^(A), CF₃, NO₂,NR^(A)R^(B), COR^(A), CO₂R^(A), OCORA, NR^(A)COR^(B), CONR^(A)R^(B); mayindependently be H; F; Cl; CN; CF₃; OH; NH₂; C₁₋₆ alkyl; C₁₋₆ amino;C₁₋₆ alkoxy; CHO; C₂₋₆—CO-alkyl; CO₂H; or C₂₋₆—CO₂-alkyl; mayindependently be H, C₁-C₃ alkyl, or C₁₋₃ perfluoroalkyl; or may be H.

With respect to any relevant structural representation, such as Formulas5, 6, 7, 8, or 9, in some embodiments R⁴⁹ is H, C₁-C₃ alkyl, or C₁₋₃perfluoroalkyl. In some embodiments, R⁴⁹ is H. In some embodiments, R⁴⁹is methyl. Additionally, for any embodiments recited in this paragraph,all remaining relevant groups of R¹⁻⁶⁰ may independently be R^(A), F,Cl, CN, OR^(A), CF₃, NO₂, NR^(A)R^(B), COR^(A), CO₂R^(A), OCORA,NR^(A)COR^(B), CONR^(A)R^(B); may independently be H; F; Cl; CN; CF₃;OH; NH₂; C₁₋₆ alkyl; C₁₋₆ amino; C₁₋₆ alkoxy; CHO; C₂₋₆—CO-alkyl; CO₂H;or C₂₋₆—CO₂-alkyl; may independently be H, C₁-C₃ alkyl, or C₁₋₃perfluoroalkyl; or may be H.

With respect to any relevant structural representation, such as Formulas5, 6, 7, 8, or 9, in some embodiments R⁵⁰ is H, C₁-C₃ alkyl, or C₁₋₃perfluoroalkyl. In some embodiments, R⁵⁰ is H. Additionally, for anyembodiments recited in this paragraph, all remaining relevant groups ofR¹⁻⁶⁰ may independently be R^(A), F, Cl, CN, OR^(A), CF₃, NO₂,NR^(A)R^(B), COR^(A), CO₂R^(A), OCORA, NR^(A)COR^(B), CONR^(A)R^(B); mayindependently be H; F; Cl; CN; CF₃; OH; NH₂; C₁₋₆ alkyl; C₁₋₆ amino;C₁₋₆ alkoxy; CHO; C₂₋₆—CO-alkyl; CO₂H; or C₂₋₆—CO₂-alkyl; mayindependently be H, C₁-C₃ alkyl, or C₁₋₃ perfluoroalkyl; or may be H.

With respect to any relevant structural representation, such as Formulas8, or 9, in some embodiments R⁵¹ is H, C₁-C₃ alkyl, or C₁₋₃perfluoroalkyl. In some embodiments, R⁵¹ is H. Additionally, for anyembodiments recited in this paragraph, all remaining relevant groups ofR¹⁻⁶⁰ may independently be R^(A), F, Cl, CN, OR^(A), CF₃, NO₂,NR^(A)R^(B), COR^(A), CO₂R^(A), OCORA, NR^(A)COR^(B), CONR^(A)R^(B); mayindependently be H; F; Cl; CN; CF₃; OH; NH₂; C₁₋₆ alkyl; C₁₋₆ amino;C₁₋₆ alkoxy; CHO; C₂₋₆—CO-alkyl; CO₂H; or C₂₋₆—CO₂-alkyl; mayindependently be H, C₁-C₃ alkyl, or C₁₋₃ perfluoroalkyl; or may be H.

With respect to any relevant structural representation, such as Formulas8 or 9, in some embodiments R⁵² is H, C₁-C₃ alkyl, or C₁₋₃perfluoroalkyl. In some embodiments, R⁵² is H. Additionally, for anyembodiments recited in this paragraph, all remaining relevant groups ofR¹⁻⁶⁰ may independently be R^(A), F, Cl, CN, OR^(A), CF₃, NO₂,NR^(A)R^(B), COR^(A), CO₂R^(A), OCORA, NR^(A)COR^(B), CONR^(A)R^(B); mayindependently be H; F; Cl; CN; CF₃; OH; NH₂; C₁₋₆ alkyl; C₁₋₆ amino;C₁₋₆ alkoxy; CHO; C₂₋₆—CO-alkyl; CO₂H; or C₂₋₆—CO₂-alkyl; mayindependently be H, C₁-C₃ alkyl, or C₁₋₃ perfluoroalkyl; or may be H.

With respect to any relevant structural representation, such as Formulas8 or 9, in some embodiments R⁵³ is H, C₁-C₃ alkyl, or C₁₋₃perfluoroalkyl. In some embodiments, R⁵³ is H. Additionally, for anyembodiments recited in this paragraph, all remaining relevant groups ofR¹⁻⁶⁰ may independently be R^(A), F, Cl, CN, OR^(A), CF₃, NO₂,NR^(A)R^(B), COR^(A), CO₂R^(A), OCORA, NR^(A)COR^(B), CONR^(A)R^(B); mayindependently be H; F; Cl; CN; CF₃; OH; NH₂; C₁₋₆ alkyl; C₁₋₆ amino;C₁₋₆ alkoxy; CHO; C₂₋₆—CO-alkyl; CO₂H; or C₂₋₆—CO₂-alkyl; mayindependently be H, C₁-C₃ alkyl, or C₁₋₃ perfluoroalkyl; or may be H.

With respect to any relevant structural representation, such as Formulas8 or 9, in some embodiments R⁵⁴ is H, C₁-C₃ alkyl, or C₁₋₃perfluoroalkyl. In some embodiments, R⁵⁴ is H. Additionally, for anyembodiments recited in this paragraph, all remaining relevant groups ofR¹⁻⁶⁰ may independently be R^(A), F, Cl, CN, OR^(A), CF₃, NO₂,NR^(A)R^(B), COR^(A), CO₂R^(A), OCORA, NR^(A)COR^(B), CONR^(A)R^(B); mayindependently be H; F; Cl; CN; CF₃; OH; NH₂; C₁₋₆ alkyl; C₁₋₆ amino;C₁₋₆ alkoxy; CHO; C₂₋₆—CO-alkyl; CO₂H; or C₂₋₆—CO₂-alkyl; mayindependently be H, C₁-C₃ alkyl, or C₁₋₃ perfluoroalkyl; or may be H.

With respect to any relevant structural representation, such as Formulas8 or 9, in some embodiments R⁵⁵ is H, C₁-C₃ alkyl, or C₁₋₃perfluoroalkyl. In some embodiments, R⁵⁵ is H. Additionally, for anyembodiments recited in this paragraph, all remaining relevant groups ofR¹⁻⁶⁰ may independently be R^(A), F, Cl, CN, OR^(A), CF₃, NO₂,NR^(A)R^(B), COR^(A), CO₂R^(A), OCORA, NR^(A)COR^(B), CONR^(A)R^(B); mayindependently be H; F; Cl; CN; CF₃; OH; NH₂; C₁₋₆ alkyl; C₁₋₆ amino;C₁₋₆ alkoxy; CHO; C₂₋₆—CO-alkyl; CO₂H; or C₂₋₆—CO₂-alkyl; mayindependently be H, C₁-C₃ alkyl, or C₁₋₃ perfluoroalkyl; or may be H.

With respect to any relevant structural representation, such as Formula9, in some embodiments R⁵⁶ is H, C₁-C₃ alkyl, or C₁₋₃ perfluoroalkyl. Insome embodiments, R⁵⁶ is H. Additionally, for any embodiments recited inthis paragraph, all remaining relevant groups of R¹⁻⁶⁰ may independentlybe R^(A), F, Cl, CN, OR^(A), CF₃, NO₂, NR^(A)R^(B), COR^(A), CO₂R^(A),OCORA, NR^(A)COR^(B), CONR^(A)R^(B); may independently be H; F; Cl; CN;CF₃; OH; NH₂; C₁₋₆ alkyl; C₁₋₆ amino; C₁₋₆ alkoxy; CHO; C₂₋₆—CO-alkyl;CO₂H; or C₂₋₆—CO₂-alkyl; may independently be H, C₁-C₃ alkyl, or C₁₋₃perfluoroalkyl; or may be H.

With respect to any relevant structural representation, such as Formula9, in some embodiments R⁵⁷ is H, C₁-C₃ alkyl, or C₁₋₃ perfluoroalkyl. Insome embodiments, R⁵⁷ is H. Additionally, for any embodiments recited inthis paragraph, all remaining relevant groups of R¹⁻⁶⁰ may independentlybe R^(A), F, Cl, CN, OR^(A), CF₃, NO₂, NR^(A)R^(B), COR^(A), CO₂R^(A),OCORA, NR^(A)COR^(B), CONR^(A)R^(B); may independently be H; F; Cl; CN;CF₃; OH; NH₂; C₁₋₆ alkyl; C₁₋₆ amino; C₁₋₆ alkoxy; CHO; C₂₋₆—CO-alkyl;CO₂H; or C₂₋₆—CO₂-alkyl; may independently be H, C₁-C₃ alkyl, or C₁₋₃perfluoroalkyl; or may be H.

With respect to any relevant structural representation, such as Formula9, in some embodiments R⁵⁸ is H, C₁-C₃ alkyl, or C₁₋₃ perfluoroalkyl. Insome embodiments, R⁵⁸ is H. Additionally, for any embodiments recited inthis paragraph, all remaining relevant groups of R¹⁻⁶⁰ may independentlybe R^(A), F, Cl, CN, OR^(A), CF₃, NO₂, NR^(A)R^(B), COR^(A), CO₂R^(A),OCORA, NR^(A)COR^(B), CONR^(A)R^(B); may independently be H; F; Cl; CN;CF₃; OH; NH₂; C₁₋₆ alkyl; C₁₋₆ amino; C₁₋₆ alkoxy; CHO; C₂₋₆—CO-alkyl;CO₂H; or C₂₋₆—CO₂-alkyl; may independently be H, C₁-C₃ alkyl, or C₁₋₃perfluoroalkyl; or may be H.

With respect to any relevant structural representation, such as Formula9, in some embodiments R⁵⁹ is H, C₁-C₃ alkyl, or C₁₋₃ perfluoroalkyl. Insome embodiments, R⁵⁹ is H. Additionally, for any embodiments recited inthis paragraph, all remaining relevant groups of R¹⁻⁶⁰ may independentlybe R^(A), F, Cl, CN, OR^(A), CF₃, NO₂, NR^(A)R^(B), COR^(A), CO₂R^(A),OCORA, NR^(A)COR^(B), CONR^(A)R^(B); may independently be H; F; Cl; CN;CF₃; OH; NH₂; C₁₋₆ alkyl; C₁₋₆ amino; C₁₋₆ alkoxy; CHO; C₂₋₆—CO-alkyl;CO₂H; or C₂₋₆—CO₂-alkyl; may independently be H, C₁-C₃ alkyl, or C₁₋₃perfluoroalkyl; or may be H.

With respect to any relevant structural representation, such as Formula9, in some embodiments R⁶⁰ is H, C₁-C₃ alkyl, or C₁₋₃ perfluoroalkyl. Insome embodiments, R⁶⁰ is H. Additionally, for any embodiments recited inthis paragraph, all remaining relevant groups of R¹⁻⁶⁰ may independentlybe R^(A), F, Cl, CN, OR^(A), CF₃, NO₂, NR^(A)R^(B), COR^(A), CO₂R^(A),OCORA, NR^(A)COR^(B), CONR^(A)R^(B); may independently be H; F; Cl; CN;CF₃; OH; NH₂; C₁₋₆ alkyl; C₁₋₆ amino; C₁₋₆ alkoxy; CHO; C₂₋₆—CO-alkyl;CO₂H; or C₂₋₆—CO₂-alkyl; may independently be H, C₁-C₃ alkyl, or C₁₋₃perfluoroalkyl; or may be H.

In one embodiment, a host compound for use in emissive elements oforganic light emitting devices is described, the compound beingrepresented by Formula 10:

HT-2 can be optionally substituted carbazoyl, optionally substitutedphenylcarbazolyl, optionally substituted (phenylcarbazolyl)phenyl, oroptionally substituted phenylnaphthylamine; and ET-3 is an optionallysubstituted benzimidazol-2-yl, an optionally substitutedbis(benzo[d]oxazol-2-yl)benz-1-yl, or an optionally substituted3,5-bis(1-phenyl-1H-benzo[d]imidazol-2-yl)benz-1-yl.

In another embodiment, HT-2 can be:

In another embodiment, ET-3 can be:

In one embodiment, a host compound for use in emissive elements oforganic light emitting devices is described, the compound beingrepresented by Formula 11:

In another embodiment, HT-3 can be an optionally substituted cabazolyl,an optionally substituted phenylcarbazolyl or an optionally substitutedphenylnaphthylaminophenyl.

In one embodiment, a host compound for use in emissive elements oforganic light emitting devices is described, the compound beingrepresented by Formula 12:

wherein X can be O, S or optionally substituted N.

In some embodiments, X can be

In other embodiments, the compound can be one of the following Hosts:

N-phenyl-N-(4′″-(1-phenyl-1H-benzo[d]imidazol-2-yl)-[1,1′:2′,1″:2″,1′″-quaterphenyl]-4-yl)naphthalen-1-amine(Host-1)

9-phenyl-3-(4″-(1-phenyl-1H-benzo[d]imidazol-2-yl)-[1,1′:2′,1″-terphenyl]-2-yl)-9H-carbazole(Host-2)

3-(3″,5″-bis(1-phenyl-1H-benzo[d]imidazol-2-yl)-[1,1′:2′,1″-terphenyl]-2-yl)-9-phenyl-9H-carbazole(Host-3)

2,2′-(2″-(9-phenyl-9H-carbazol-3-yl)[1,1′:2′,1″-terphenyl]-3,5-diyl)bis(benzo[d]oxazole)(Host-4)

3-(4″-(1-phenyl-1H-benzo[d]imidazol-2-yl)-[1,1′:2′,1″-terphenyl]-2-yl)-9-(p-tolyl)-9H-carbazole(Host-5)

9-phenyl-3-(4′″-(1-phenyl-1H-benzo[d]imidazol-2-yl)-[1,1′:2′,1″:2″,1′″-quaterphenyl]-4-yl)-9H-carbazole(Host-6)

In another embodiment, an emissive element is described comprising anyof the aforementioned compounds.

In another embodiment, a device is described comprising any of theaforementioned compounds.

As shown in FIGS. 1 and 2, there are shown embodiments of organic lightemitting devices incorporating the compounds of the present application.The embodiments also provide an organic light-emitting diode device 10comprising a cathode 20, an anode 30, a light-emitting layer 40 disposedbetween and electrically connected to the anode and the cathode, ahole-transport layer 50 between the anode and the light-emitting layer40 and an electron-transport layer 60 between the cathode 30 and thelight-emitting layer 40, wherein at least one of the light-emittinglayer, the hole-transport layer and the electron-transport layercomprise a host compound described herein. In some embodiments, a holeinjection layer 70 can be between the anode 20 and the hole transportlayer 50.

An anode layer may comprise a conventional material such as a metal,mixed metal, alloy, metal oxide or mixed-metal oxide, or a conductivepolymer. Examples of suitable metals include the Group 1 metals, themetals in Groups 4, 5, 6, and the Group 8-10 transition metals. If theanode layer is to be light-transmitting, mixed-metal oxides of Group 12,13, and 14 metals or alloys thereof, such as Au, Pt, andindium-tin-oxide (ITO), may be used. The anode layer may include anorganic material such as polyaniline, e.g., as described in “Flexiblelight-emitting diodes made from soluble conducting polymer,” Nature,vol. 357, pp. 477-479 (11 Jun. 1992). Examples of suitable high workfunction metals include but are not limited to Au, Pt, indium-tin-oxide(ITO), or alloys thereof. In some embodiments, the anode layer can havea thickness in the range of about 1 nm to about 1000 nm.

A cathode layer may include a material having a lower work function thanthe anode layer. Examples of suitable materials for the cathode layerinclude alkali metals of Group 1, Group 2 metals, Group 12 metalsincluding rare earth elements, lanthanides and actinides, materials suchas aluminum, indium, calcium, barium, samarium and magnesium, andcombinations thereof. Li-containing organometallic compounds, LiF, andLi₂O may also be deposited between the organic layer and the cathodelayer to lower the operating voltage. Suitable low work function metalsinclude but are not limited to Al, Ag, Mg, Ca, Cu, Mg/Ag, LiF/Al, CsF,CsF/Al or alloys thereof. In some embodiments, the cathode layer canhave a thickness in the range of about 1 nm to about 1000 nm.

In some embodiments, the light-emissive layer may further comprise anemissive component or compound. The emissive component may be afluorescent and/or a phosphorescent compound. In some embodiments, theemissive component comprises a phosphorescent material. In someembodiments, the emissive component may comprise a dopant. In someembodiments, the dopant is up to about 10% (w/w) of the host, or fromabout 0.1% (w/w) to about 5% (w/w) of the host.

The thickness of the light-emitting layer may vary. In some embodiments,the light-emitting layer has a thickness from about 20 nm to about 200nm. In some embodiments, the light-emitting layer has a thickness in therange of about 20 nm to about 150 nm.

In some embodiments, the light-emitting layer can further includeadditional host material. Exemplary host materials are known to thoseskilled in the art. For example, the host material included in thelight-emitting layer can be an optionally substituted compound selectedfrom: an aromatic-substituted amine, an aromatic-substituted phosphine,a thiophene, an oxadiazole,2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (PBD),1,3-bis(N,N-t-butyl-phenyl)-1,3,4-oxadiazole (OXD-7), a triazole,3-phenyl-4-(1′-naphthyl)-5-phenyl-1,2,4-triazole (TAZ),3,4,5-triphenyl-1,2,3-triazole,3,5-bis(4-tert-butyl-phenyl)-4-phenyl[1,2,4]triazole, an aromaticphenanthroline, 2,9-dimethyl-4,7-diphenyl-phenanthroline (bathocuproineor BCP), 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline, a benzoxazole, abenzothiazole, a quinoline, aluminum tris(8-hydroxyquinolate) (Alq3), apyridine, a dicyanoimidazole, cyano-substituted aromatic,1,3,5-tris(2-N-phenylbenzimidazolyl)benzene (TPBI),4,4′-bis[N-(naphthyl)-N-phenyl-amino]biphenyl (α-NPD),N,N′-bis(3-methylphenyl)N,N′-diphenyl-[1,1′-biphenyl]-4,4′-diamine(TPD), 4,4′-bis[N,N′-(3-tolyl)amino]-3,3′-dimethylbiphenyl (M14),4,4′-bis[N,N′-(3-tolyl)amino]-3,3′-dimethylbiphenyl (HMTPD),1,1-bis(4-bis(4-methylphenyl)aminophenyl)cyclohexane, a carbazole,4,4′-N,N′-dicarbazole-biphenyl (CBP), poly(9-vinylcarbazole) (PVK),N,N′N″-1,3,5-tricarbazoloylbenzene (tCP), a polythiophene, a benzidine,N,N′-bis(4-butylphenyl)-N,N′-bis(phenyl)benzidine, a triphenylamine,4,4′,4″-tris(N-(naphthylen-2-yl)-N-phenylamino)triphenylamine,4,4′,4″-tris(3-methylphenylphenylamino)triphenylamine (MTDATA), aphenylenediamine, a polyacetylene, and a phthalocyanine metal complex.

In some embodiments, the light-emitting device may further comprise ahole-transport layer between the anode and the light-emitting layer andan electron-transport layer between the cathode and the light-emittinglayer. In some embodiments, all of the light-emitting layer, thehole-transport layer and the electron-transport layer comprise the hostcompound described herein.

In some embodiments, the hole-transport layer may comprise at least onehole-transfer materials. Suitable hole-transport materials are known tothose skilled in the art. Exemplary hole-transport materials include:1,1-bis(4-bis(4-methylphenyl)aminophenyl)cyclohexane;2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline;3,5-bis(4-tert-butyl-phenyl)-4-phenyl[1,2,4]triazole;3,4,5-triphenyl-1,2,3-triazole;4,4′,4″-tris(N-(naphthylen-2-yl)-N-phenylamino)triphenylamine;4,4′,4′-tris(3-methylphenylphenylamino)triphenylamine (MTDATA);4,4′-bis[N-(naphthyl)-N-phenyl-amino]biphenyl (α-NPD);4,4′-bis[N,N′-(3-tolyl)amino]-3,3′-dimethylbiphenyl (HMTPD);4,4′-bis[N,N′-(3-tolyl)amino]-3,3′-dimethylbiphenyl (M14);4,4′-N,N′-dicarbazole-biphenyl (CBP); 1,3-N,N-dicarbazole-benzene (mCP);poly(9-vinylcarbazole) (PVK); a benzidine; a carbazole; aphenylenediamine; a phthalocyanine metal complex; a polyacetylene; apolythiophene; a triphenylamine; an oxadiazole; copper phthalocyanine;N,N′-bis(3-methylphenyl)N,N′-diphenyl-[1,1′-biphenyl]-4,4′-diamine(TPD); N,N′N″-1,3,5-tricarbazoloylbenzene (tCP);N,N′-bis(4-butylphenyl)-N,N′-bis(phenyl)benzidine;4,4′-bis[N-(1-napthyl)-N-phenylamino]biphenyl (NPB),4,4′4″-tri(N-carbazolyl)triphenylamine (TcTa) and the like.

In some embodiments, the electron-transport layer may comprise at leastone electron-transfer materials. Suitable electron transport materialsare known to those skilled in the art. Exemplary electron transportmaterials that can be included in the electron transport layer are anoptionally substituted compound selected from: aluminumtris(8-hydroxyquinolate) (Alq₃),2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (PBD),1,3-bis(N,N-t-butyl-phenyl)-1,3,4-oxadiazole (OXD-7),1,3-bis[2-(2,2′-bipyridine-6-yl)-1,3,4-oxadiazo-5-yl]benzene (BPY-OXD),3-phenyl-4-(1′-naphthyl)-5-phenyl-1,2,4-triazole (TAZ),2,9-dimethyl-4,7-diphenyl-phenanthroline (bathocuproine or BCP), and1,3,5-tris[2-N-phenylbenzimidazol-z-yl]benzene (TPBI). In oneembodiment, the electron transport layer is aluminum quinolate (Alq₃),2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (PBD),phenanthroline, quinoxaline,1,3,5-tris[N-phenylbenzimidazol-z-yl]benzene (TPBI), or a derivative ora combination thereof.

If desired, additional layers may be included in the light-emittingdevice. Additional layers that may be included include an electroninjection layer (EIL), hole blocking layer (HBL), exciton blocking layer(EBL), and/or hole injection layer (HIL). In addition to separatelayers, some of these materials may be combined into a single layer.

In some embodiments, the light-emitting device can include an electroninjection layer between the cathode layer and the light emitting layer.In some embodiments, the lowest un-occupied molecular orbital (LUMO)energy level of the material(s) that can be included in the electroninjection layer is high enough to prevent it from receiving an electronfrom the light emitting layer. In other embodiments, the energydifference between the LUMO of the material(s) that can be included inthe electron injection layer and the work function of the cathode layeris small enough to allow efficient electron injection from the cathode.A number of suitable electron injection materials are known to thoseskilled in the art. Examples of suitable material(s) that can beincluded in the electron injection layer include but are not limited to,an optionally substituted compound selected from the following: aluminumquinolate (Alq₃),2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (PBD),phenanthroline, quinoxaline,1,3,5-tris[N-phenylbenzimidazol-z-yl]benzene (TPBI) a triazine, a metalchelate of 8-hydroxyquinoline such as tris(8-hydroxyquinoliate)aluminum, and a metal thioxinoid compound such asbis(8-quinolinethiolato) zinc. In one embodiment, the electron injectionlayer is aluminum quinolate (Alq₃),2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (PBD),phenanthroline, quinoxaline,1,3,5-tris[N-phenylbenzimidazol-z-yl]benzene (TPBI), or a derivative ora combination thereof.

In some embodiments, the device can include a hole blocking layer, e.g.,between the cathode and the light-emitting layer. Various suitable holeblocking materials that can be included in the hole blocking layer areknown to those skilled in the art. Suitable hole blocking material(s)include, but are not limited to, an optionally substituted compoundselected from the following: bathocuproine (BCP),3,4,5-triphenyl-1,2,4-triazole,3,5-bis(4-tert-butyl-phenyl)-4-phenyl-[1,2,4]triazole,2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline, and1,1-bis(4-bis(4-methylphenyl)aminophenyl)-cyclohexane.

In some embodiments, the light-emitting device can include an excitonblocking layer, e.g., between the light-emitting layer and the anode. Inone embodiment, the band gap of the material(s) that comprise excitonblocking layer is large enough to substantially prevent the diffusion ofexcitons. A number of suitable exciton blocking materials that can beincluded in the exciton blocking layer are known to those skilled in theart. Examples of material(s) that can compose an exciton blocking layerinclude an optionally substituted compound selected from the following:aluminum quinolate (Alq₃), 4,4′-bis[N-(naphthyl)-N-phenyl-amino]biphenyl(α-NPD), 4,4′-N,N′-dicarbazole-biphenyl (CBP), and bathocuproine (BCP),and any other material(s) that have a large enough band gap tosubstantially prevent the diffusion of excitons.

In some embodiments, the light-emitting device can include a holeinjection layer, e.g., between the light-emitting layer and the anode.Various suitable hole injection materials that can be included in thehole injection layer are known to those skilled in the art. Exemplaryhole injection material(s) include an optionally substituted compoundselected from the following: a polythiophene derivative such aspoly(3,4-ethylenedioxythiophene (PEDOT)/polystyrene sulphonic acid(PSS), a benzidine derivative such as N,N,N′,N′-tetraphenylbenzidine,poly(N,N′-bis(4-butylphenyl)-N,N′-bis(phenyl)benzidine), atriphenylamine or phenylenediamine derivative such asN,N′-bis(4-methylphenyl)-N,N′-bis(phenyl)-1,4-phenylenediamine,4,4′,4″-tris(N-(naphthylen-2-yl)-N-phenylamino)triphenylamine, anoxadiazole derivative such as1,3-bis(5-(4-diphenylamino)phenyl-1,3,4-oxadiazol-2-yl)benzene, apolyacetylene derivative such as poly(1,2-bis-benzylthio-acetylene), anda phthalocyanine metal complex derivative such as phthalocyanine copper.Hole-injection materials, while still being able to transport holes, mayhave a hole mobility substantially less than the hole mobility ofconventional hole transport materials.

Those skilled in the art would recognize that the various materialsdescribed above can be incorporated in several different layersdepending on the configuration of the device. In one embodiment, thematerials used in each layer are selected to result in the recombinationof the holes and electrons in the light-emitting layer.

Light-emitting devices comprising the compounds disclosed herein can befabricated using techniques known in the art, as informed by theguidance provided herein. For example, a glass substrate can be coatedwith a high work functioning metal such as ITO which can act as ananode. After patterning the anode layer, a light-emitting layer thatincludes at least a compound disclosed herein can be deposited on theanode. The cathode layer, comprising a low work functioning metal (e.g.,Mg:Ag), can then be vapor evaporated onto the light-emitting layer. Ifdesired, the device can also include an electron transport/injectionlayer, a hole blocking layer, a hole injection layer, an excitonblocking layer and/or a second light-emitting layer that can be added tothe device using techniques known in the art, as informed by theguidance provided herein.

EXAMPLES Example 1 Luminescent Dye Synthesis of Bipolar Hosts

2-(4-bromophenyl)-1-phenyl-1H-benzo[d]imidazole (Compound 1)

Compound 1 (Ge, Z.; Hayakawa, T.; Ando, S.; Ueda, M.; Akiike, T.;Miyamoto, H.; Kajita, T.; Kakimoto, M. Chem. Mater. 2008, 20(7),2532-2537) was prepared as follows: to a chilled (ca. 0° C.), stirringsolution of N-phenyl-o-phenylene-1,2-diamine (21.41 g, 116.2 mmol) inanhydrous dichloromethane (CH₂Cl₂) (575 mL) was added 4-bromobenzoylchloride (25.00 g, 113.9 mmol) portion-wise, followed by dropwiseaddition of triethylamine (Et₃N) (31.8 mL). The reaction was allowed towarm to room temperature and stirring continued until TLC (SiO₂, 4:1hexanes-ethyl acetate) indicated consumption of the starting material.Upon completion, the reaction was washed with water and brine, driedover MgSO₄, filtered and concentrated in vacuo. The resulting crude wasthen dissolved in anhydrous 1,4-dioxane (500 mL) and heated to about 80°C. Upon completely dissolving, phosphorus oxychloride (31.2 mL, 335mmol) was added to the solution slowly via syringe and the reaction thenmaintained at about 115° C. Upon completion (ca. 1 h), the solution wascooled to room temperature (RT) and poured over CH₂Cl₂ (ca. 3 L) andwashed with brine. The organics were then dried over MgSO₄, filtered andconcentrated in vacuo. Purification of the crude product byrecrystallization from CH₂Cl₂ and hexanes provided Compound 1 (37.5 g,94%) as an off-white solid: confirmed by LCMS (APCI): calculated forC₁₉H₁₃BrN₂ (M⁺): 349; Found: 349.

1-phenyl-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1H-benzo[d]imidazole(Compound 2)

A procedure from the literature [Ge, Z.; Hayakawa, T.; Ando, S.; Ueda,M.; Akiike, T.; Miyamoto, H.; Kajita, T.; Kakimoto, M. Chem. Mater.2008, 20(7), 2532-2537] was modified as follows: a mixture of Compound 1(36.00 g, 103.1 mmol), bis(pinacolato)diboron (28.80 g, 113.4 mmol),[1,1′-bis(diphenylphosphino)-ferrocene]dichloropalladium(II) (3.771 g,5.154 mmol), potassium acetate (30.35 g, 309.3 mmol) and 1,4-dioxane(480 mL) was degassed with argon for about 1 h at about 40° C. whilestirring. The reaction mixture was then maintained under argon at about80° C. while stirring. Upon confirming consumption of the startingmaterial by TLC (SiO₂, 9:1 hexanes-ethyl acetate), the reaction wascooled to RT and poured over ethyl acetate (EtOAc) (ca. 1.6 L). Themixture was then filtered through a short silica gel plug (ca. ½ inch)and the filtrant washed copiously with EtOAc (ca. 200 mL). The combinedorganics were then washed with sat. NaHCO₃, water and brine, dried overMgSO₄, filtered and concentrated in vacuo. Purification of the crudeproduct via flash chromatography (SiO₂, 4:1 to 1:1-hexanes:ethylacetate) afforded Compound 2 (36.8 g, 90%) as an off-white powder:confirmed by LCMS (APCI): calculated for C₂₅H₂₆BN₂O₂ (M+H⁺): 397; Found:397.

2-(2″-bromo-[1,1′:2′,1″-terphenyl]-4-yl)-1-phenyl-1H-benzo[d]imidazole(Compound 3)

A mixture of Compound 2 (3.00 g, 7.57 mmol), 2,2′-dibromo-1,1′-biphenyl(4.72 g, 15.1 mmol), tetrakis(triphenylphosphine)palladium(0) (0.350 g,0.303 mmol), Na₂CO₃ (3.18 g, 30.0 mmol), H₂O (30 mL) and tetrahydrofuran(THF) (50 mL) was degassed with argon for about 44 min while stirring.The reaction mixture was then maintained under argon at about 80° C.while stirring. Upon confirming consumption of the starting material byTLC (SiO₂, 19:1—CH₂Cl₂:acetone), the reaction was cooled to RT andpoured over CH₂Cl₂ (ca. 250 mL). The organics were then washed with H₂Oand brine, dried over MgSO₄, filtered and concentrated in vacuo. Thecrude product was purified via flash chromatography (SiO₂, 100% CH₂Cl₂to 39:1—CH₂Cl₂:acetone) to yield Compound 3 (2.34 g, 62%) as anoff-white foam: confirmed by LCMS (APCI): calculated for C₃₁H₂₁BrN₂(M⁺): 501; Found: 501.

N-(4-bromophenyl)-N-phenylnaphthalen-1-amine (Compound 4)

Compound 4 [Xu, H.; Yin, K.; Huang, W. Chem. Eur. J. 2007, 13(36),10281-10293] was prepared as follows: a mixture ofN-phenylnaphthalen-1-amine (2.767 g, 12.62 mmol), 1-bromo-4-iodobenzene(7.140 g, 25.24 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.578g, 0.631 mmol), tri-tert-butylphosphine (10 wt. % in hexanes) (5.83 mL,1.89 mmol), sodium tert-butoxide (NaOtBu) (3.032 g, 31.55 mmol) andanhydrous toluene (80 mL) was degassed with argon for about 40 min whilestirring. The reaction mixture was then maintained under argon at about85° C. while stirring. Upon confirming consumption of the startingmaterial by TLC (SiO₂, 100% hexanes), the reaction was cooled to RT andpoured over EtOAc (ca. 300 mL). The organics were then washed with sat.NaHCO₃, H₂O (2×) and brine, dried over MgSO₄, filtered and concentratedin vacuo. Purification of the crude product via flash chromatography(SiO₂, 8:1-hexanes:CH₂Cl₂) provided Compound 4 (2.93 g, 62%) as a whitefoam: confirmed by LCMS (APCI): calculated for C₂₂H₁₆BrN (M⁺): 374;Found: 374.

N-phenyl-N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)naphthalen-1-amine(Compound 5)

Compound 5 [Shin, D.; Paek, W.; Choi, B.; Kwon, 0.; Kim, M.; Son, Y.;Han, E.; Song, J. U.S. Pat. Appl. Publ., 20070276160, 29 Nov. 2007] wasprepared as follows: a mixture of Compound 4 (2.54 g, 6.79 mmol),bis(pinacolato)diboron (3.62 g, 14.3 mmol),[1,1′-bis(diphenylphosphino)-ferrocene]dichloropalladium(II) (0.298 g,0.407 mmol), potassium acetate (2.00 g, 20.4 mmol) and anhydrous toluene(50 mL) was degassed with argon for about 28 min while stirring. Thereaction mixture was then maintained under argon at about 100° C. whilestirring. Upon confirming consumption of the starting material by TLC(SiO₂, 4:1 hexanes—CH₂Cl₂), the reaction was cooled to RT and pouredover EtOAc (ca. 200 mL). The organics were then washed with sat. NaHCO₃,water and brine, dried over MgSO₄, filtered and concentrated in vacuo.Purification of the crude product via flash chromatography (SiO₂, 2:1 to3:2-hexanes: CH₂Cl₂ to 100% CH₂Cl₂) yielded Compound 5 (2.78 g, 97%) asa colorless foam: confirmed by LCMS (APCI): calculated for C₂₈H₂₉BNO₂(M+H⁺): 422; Found: 422.

N-phenyl-N-(4′″-(1-phenyl-1H-benzo[d]imidazol-2-yl)-[1,1′:2′,1″:2″,1′″-quaterphenyl]-4-yl)naphthalen-1-amine(Host-1)

A mixture of Compound 5 (0.588 g, 1.40 mmol), Compound 3 (0.700 g, 1.40mmol), tetrakis(triphenylphosphine)palladium(0) (64.5 mg, 55.8 μmol),Na₂CO₃ (0.530 g, 5.00 mmol), H₂O (5 mL) and 1,4-dioxane (25 mL) wasdegassed with argon for about 18 min while stirring. The reactionmixture was then maintained under argon at about 110° C. while stirring.Upon confirming consumption of the starting material by LCMS, thereaction was cooled to RT and poured over CH₂Cl₂ (ca. 300 mL). Theorganics were then washed with H₂O and brine, dried over MgSO₄, filteredand concentrated in vacuo. The crude product was purified via flashchromatography (SiO₂, 17:3-hexanes: acetone) and recrystallization fromCH₃OH to afford Host-1 (0.97 g, 85%) as an off-white solid: confirmed byLCMS (APCI): calculated for C₅₃H₃₇N₃ (M⁺): 716; Found: 716.

9-phenyl-3-(4″-(1-phenyl-1H-benzo[d]imidazol-2-yl)-[1,1′:2′,1″-terphenyl]-2-yl)-9H-carbazole(Host-2)

Following the procedure for Host-1, (9-phenyl-9H-carbazol-3-yl)boronicacid (0.458 g, 1.60 mmol), Compound 3 (0.800 g, 1.60 mmol),tetrakis(triphenylphosphine)palladium(0) (73.7 mg, 63.8 pmol), Na₂CO₃(0.530 g, 5.00 mmol), H₂O (5 mL) and 1,4-dioxane (25 mL) provided Host-2(0.78 g, 74%) as an off-white solid after flash chromatography (SiO₂,17:3-hexanes: acetone) and recrystallization from methanol (CH₃OH):confirmed by LCMS (APCI): calculated for C₄₉H₃₃N₃ (M⁺): 664; Found: 664.

5-Bromo-N1,N3-bis(2-(phenylamino)phenyl)isophthalamide (Compound 6)

A mixture of 5-bromoisophthalic acid (15.0 g, 61.2 mmol) in thionylchloride (60 mL) with 0.2 mL dimethylformamide (DMF) was heated toreflux overnight under argon. After removing the excess thionyl chlorideunder reduced pressure, the remaining liquid was dissolved in anhydrousCH₂Cl₂ (200 mL). To the solution was added N-phenyl-o-phenyldiamine(22.5 g, 122 mmol), followed by slow addition of triethylamine (22.2 mL,159 mmol) with ice-bath cooling. The mixture was allowed to warm to RTovernight. The resulting suspension was then diluted with CH₂Cl₂ (200mL), filtered and the filtrant washed with CH₂Cl₂ to provide Compound 6(30.3 g, 86%) as an off-white solid: confirmed by LCMS (APCI):calculated for C₃₂H₂₅BrN₄O₂ (M⁺): 577; Found: 577.

2,2′-(5-bromo-1,3-phenylene)bis(1-phenyl-1H-benzo[d]imidazole) (Compound7)

To a suspension of Compound 6 (30 g, 52 mmol) in anhydrous 1,4-dioxane(300 mL), POCl₃ (30.6 g, 18.6 mL, 200 mmol) was added slowly with waterbath cooling. The resulting mixture was then maintained at 100° C. Aftercooling to room temperature, the mixture was poured into ice (ca. 300 g)and neutralized with Na₂CO₃, followed by extraction with CH₂Cl₂ (2×300mL). The organic phase was then washed with brine, dried over Na₂SO₄ andconcentrated in vacuo. To the mixture, acetonitrile (300 mL) was addedand stirred, then filtered. The solid was collected and recrystallizedin CH₂Cl₂/hexane to afford a white solid (18.9 g). The filtrant waspurified by flash chromatography (SiO₂, 100% hexanes to 9:1 to4:1-hexanes/ethyl acetate). The main fraction was collected andconcentrated to give additional product, white solid (5.17 g). Totalamount is 24.1 g (86%): confirmed by LCMS (APCI): calculated forC₃₂H₂₁BrN₄ (M⁺): 541; Found: 541.

2,2′-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3-phenylene)bis(1-phenyl-1H-benzo[d]imidazole)(Compound 8)

A mixture of Compound 7 (10.0 g, 18.5 mmol), bis(pinacolato)diboron (5.0g, 20 mmol), PdCl₂(dppf) (0.50 g, 0.68 mmol) and potassium acetate (10.0g, 102 mmol) in anhydrous 1,4-dioxane (300 mL) was degassed with Ar andmaintained at about 80° C. for about 30 hours. The mixture was thenpoured over ethyl acetate (300 mL) and the organics washed with brine,dried over Na₂SO₄ and concentrated in vacuo. Purification of the crudeby flash chromatography (SiO₂, 7:3-hexanes:CH₂Cl₂) afforded Compound 8(6.58 g, 60%) as a light yellow solid: confirmed by LCMS (APCI):calculated for C₃₈H₃₄BN₄O₂ (M+H⁺): 589; Found: 589.

3-(2′-bromo-[1,1′-biphenyl]-2-yl)-9-phenyl-9H-carbazole (Compound 9)

Following the procedure for Compound 3,(9-phenyl-9H-carbazol-3-yl)boronic acid (1.84 g, 6.41 mmol),2,2′-dibromo-1,1′-biphenyl (4.00 g, 12.8 mmol),tetrakis(triphenylphosphine)palladium(0) (0.296 g, 0.257 mmol), Na₂CO₃(2.54 g, 24.0 mmol), H₂O (24 mL) and THF (40 mL) yielded Compound 9(1.69 g, 56%) as a colorless solid after flash chromatography (SiO₂,19:1-hexanes: CH₂Cl₂): confirmed by LCMS (APCI): calculated forC₃₀H₂₀NBr (M⁺): 474; Found: 474.

3-(3″,5″-bis(1-phenyl-1H-benzo[d]imidazol-2-yl)-[1,1′:2′,1″-terphenyl]-2-yl)-9-phenyl-9H-carbazole(Host-3)

Following the procedure for Host-1, Compound 8 (0.992 g, 1.69 mmol),Compound 9 (0.800 g, 1.69 mmol),tetrakis(triphenylphosphine)palladium(0) (77.9 mg, 67.5 μmol), Na₂CO₃(0.530 g, 5.00 mmol), H₂O (5 mL) and 1,4-dioxane (25 mL) yielded Host-3(1.15 g, 79%) as an off-white solid after flash chromatography (SiO₂,100% CH₂Cl₂ to 19:1—CH₂Cl₂:acetone): confirmed by LCMS (APCI):calculated for C₆₂H₄₁N₅ (M⁺): 856; Found: 856.

5-bromo-N1,N3-bis(2-bromophenyl)isophthalamide (Compound 10)

A mixture of 5-bromoisophthalic acid (10.0 g, 40.8 mmol) and cat. DMF (5drops) in thionyl chloride (40 mL, 551 mmol) was heated to reflux underAr overnight. After removal of the excess thionyl chloride under vacuum,the crude intermediate was dissolved in anhydrous CH₂Cl₂ (200 mL). Tothe chilled (0° C.) solution was added 2-bromoaniline (14.0 g, 81.6mmol), followed by dropwise addition of triethylamine (15 mL). Theresulting mixture was then stirred overnight and allowed to warm to RT.The suspension was then filtered and the filtrant washed with CH₂Cl₂ toafford crude Compound 10 (20.3 g, 90%) as an off-white solid: confirmedby LCMS (APCI): calculated for C₂₀H₁₃Br₃N₂O₂ (M⁺): 553; Found: 553.

2,2′-(5-bromo-1,3-phenylene)bis(benzo[d]oxazole) (Compound 11)

A mixture of Compound 10 (20.3 g, 36.7 mmol), CuI (0.700 g, 3.67 mmol),Cs₂CO₃ (23.9 g, 73.5 mmol), 1,10-phenanthroline (1.32 g, 7.35 mmol) and1,4-dioxane (300 mL) was degassed with Ar and then maintained at about120° C. overnight. Upon confirming consumption of the starting materialby TLC (SiO₂, 4:1 hexanes-ethyl acetate), the reaction was cooled to RTand diluted with EtOAc (ca. 300 mL) and H₂O (ca. 400 mL). The resultingsuspension was then filtered and the filtrant washed copiously with H₂Oand CH₃OH to provide Compound 11 (12.7 g, 88%) as an off-white solid:confirmed by LCMS (APCI): calculated for C₂₀H₁₁BrN₂O₂ (M⁺): 391; Found:391.

2,2′-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3-phenylene)bis(benzo[d]oxazole)(Compound 12)

A mixture of Compound 11 (10.0 g, 25.6 mmol), bis(pinacolato)diboron(7.14 g, 28.1 mmol),[1,1′-bis(diphenylphosphino)-ferrocene]dichloropalladium(II) (0.935 g,1.28 mmol), potassium acetate (7.53 g, 76.7 mmol) and 1,4-dioxane (125mL) was degassed with Ar and then maintained under Ar at about 80° C.while stirring. Upon confirming consumption of the starting material byTLC (SiO₂, 4:1 hexanes-ethyl acetate), the reaction was cooled to RT andpoured over EtOAc and brine. The mixture was then filtered and thefiltrant washed copiously with H₂O to afford Compound 12 (10.2 g, 91%)as a grey solid: confirmed by LCMS (APCI): calculated for C₂₆H₂₄BN₂O₄(M+H⁺): 439; Found: 439.

2,2′-(2″-(9-phenyl-9H-carbazol-3-yl)[1,1′:2′,1″-terphenyl]-3,5-diyl)bis(benzo[d]oxazole)(Host-4)

Following the procedure for Host-1, Compound 9 (0.800 g, 1.69 mmol),Compound 12 (0.739 g, 1.69 mmol),tetrakis(triphenylphosphine)palladium(0) (77.9 mg, 67.5 μmol), Na₂CO₃(0.530 g, 5.00 mmol), H₂O (5 mL) and 1,4-dioxane (25 mL) yielded Host-4(0.89 g, 75%) as an off-white solid after flash chromatography (SiO₂,1:1 to 3:1 to 9:1—CH₂Cl₂:hexanes): confirmed by LCMS (APCI): calculatedfor C₅₀H₃₂N₃O₂ (M+H⁺): 707; Found: 707.

3-bromo-9-(p-tolyl)-9H-carbazole (Compound 13)

To a solution of 9-p-tolyl-9H-carbazole (0.82 g, 3.2 mmol) indichloromethane (DCM)(30 mL) was added N-bromosuccinimide (NBS) at about0° C. The whole was stirred at about 0° C. to about room temperature(RT) overnight. The resulting solution was purified by flash column(silica gel, hexanes to hexanes/dichloromethane 8:1). After removal ofsolvent, a white solid (Compound 13) was obtained (1.0 gram, in 93%yield).

3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9-(p-tolyl)-9H-carbazole(Compound 14): The mixture of 3-bromo-9-(p-tolyl)-9H-carbazole (Compound13)

(1.0 g, 3 mmol), bis(pinacolato)diboron (0.838 g, 3.3 mmol), KOAc (0.588g, 6 mmol) and Pd(dppf)Cl₂ (0.11 g, 0.15 mmol) in dioxane (20 mL), wasdegassed and heated at about 95° C. for about 5 hours. The resultingmixture was poured into ethyl acetate (200 mL), washed with brine, driedover Na₂SO₄, loaded on silica gel, and purified by flash column (silicagel, hexanes/dichloromethane 9:1 to 4:1 to 3:1). The desired fractionswere collected, after removal of solvents, a white solid (Compound 14)was obtained (0.60 g, in 52% yield).

Host-5:

A mixture of3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9-(p-tolyl)-9H-carbazole(Compound 14) (0.60 g, 1.57 mmol),2-(2″-bromo-[1,1′:2′,1″-terphenyl]-4-yl)-1-phenyl-1H-benzo[d]imidazole(Compound 3) (0.78 g, 1.57 mmol), Pd(PPh₃)₄ (0.092 g, 0.08 mmol) andCs₂CO₃ (0.977 g, 3 mmol) in dioxane/water (50 mL/10 mL) was degassed andheated at about 100° C. overnight. The resulting mixture was poured intoethyl acetate (200 mL), washed with brine, dried over Na₂SO₄, loaded onsilica gel and purified by flash column (hexanes/dichloromethane 4:1 todichloromethane to dichloromethane/ethyl acetate 50:1). The desiredfraction was collected, concentrated and recrystallized indichloromethane/methanol to give a white solid (Host-5) (0.85 g, in 80%yield). Confirmed by LCMS (APCI+): calculated for C₅₀H₃₆N₃ (M+H): 678;Found: 678.

3-(4-bromophenyl)-9-phenyl-9H-carbazole (Compound 15)

A mixture of9-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole(Compound 14) (5.0 g, 13.5 mmol), 4-bromoiodobenzene (10.76 g, 38 mmol),Pd(PPh₃)₄ (0.5 g, 0.43 mmol) and potassium carbonate (K₂CO₃)(5.52 g, 40mmol) in dioxane/water (80 mL/15 mL) was degassed and heated at about100° C. overnight, then worked up with ethyl acetate/brine. The organicphase was collected, dried over Na₂SO₄, and purified by flash column(hexanes to hexane/ethyl acetate 90:1). The main fraction was collected,concentrated, and a precipitate was filtered to give a white solid(Compound 15) (2.35 g, in 44% yield). Confirmed by LCMS (APCI):calculated for C₂₄H₁₇BrN (M+H): 398; Found: 398.

9-phenyl-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-9H-carbazole(Compound 16)

a mixture of compound 19 (2.33 g, 5.85 mmol), bis(pinacolate)diborane(1.524 g, 6 mmol), Pd(dppf)Cl₂ (0.22 g, 0.3 mmol) and potassiumcarbonate (3.0 g, 30 mmol) in dioxane (100 mL) was degassed and heatedat about 80° C. overnight. The mixture was worked up with ethylacetate/brine and the organic phase was collected, dried over Na₂SO₄,purified by flash column (hexanes to hexane/ethyl acetate 90:1 to 40:1to 30:1). The main fraction was collected, and white solid (Compound 20)was obtained after removal of solvent (1.94 g, in 74.5% yield).Confirmed by LCMS (APCI): calculated for C₃₀H₂₉BNO₂ (M+H): 446; Found:446.

Host-6:

A mixture of compound 20 (0.70 g, 1.57 mmol),2-(2″-bromo-[1,1′:2′,1″-terphenyl]-4-yl)-1-phenyl-1H-benzo[d]imidazole(Compound 3) (0.787 g, 1.57 mmol), Pd(PPh₃)₄ (0.115 g, 0.1 mmol) andCs₂CO₃ (0.977 g, 3 mmol) in dioxane/water (50 mL/10 mL) was degassed andheated at about 100° C. overnight. The mixture was diluted with ethylacetate (200 mL), washed with brine, dried over Na₂SO₄, loaded on silicagel and purified by flash column (hexanes/dichloromethane 4:1 todichloromethane to dichloromethane/ethyl acetate 100:1). After removalof solvent, recrystallization in dichloromethane/methanol gave a whitesolid (Host-6) (0.72 g, in 62% yield). Confirmed by LCMS (APCI+):calculated for C₅₅H₃₈N₃ (M+H): 740; Found: 740.

Physical Properties of Hosts Analytic Examples Measuring Charge Mobility

The carrier mobility of an organic thin film was derived from the spacecharge limited current in the current-voltage (IV) measurement based onthe Mott's steady state SCLC model

$J = \frac{9{ɛɛ}_{0}\mu \; V^{2}}{8L^{3}}$

where ε₀ is the vacuum permittivity, ε is the relative permittivity ofthe organic layer, μ is the carrier mobility of the organic layer, V isthe voltage bias and L is the thickness of the organic layer.

To evaluate the electron and hole mobility of an organic layer,single-carrier devices (electron-only and hole-only devices) were made.Electron-only devices may have Al/organic layer/LiF/Al structure with Alas the anode and LiF/Al as the cathode. The LiF/Al electrode has a lowwork function (˜2.6 eV) which can facilitate the injection of electronsinto the lower lying LUMO of the organic layer. By contrast, Al has arelatively lower work function (4.28 eV) than the HOMO (5˜6 eV) of theorganic layer being investigated, which prevents the hole injection fromthe anode. Thus, only electrons are injected into the organic layer andthe electron mobility may be measured as the only charge carrier in theorganic layer.

The hole-only devices may have the ITO/PEDOT/organic layer/Al with ITOas the anode and Al as the cathode. The high work function of PEDOT(5.2-5.4 eV) facilitates hole injection from the anode into the organiclayer. By contrast, the work function (4.28 eV) of Al is higher than theLUMO of the organic layer (2˜4 eV), which prevented electron injectionfrom the cathode. Thus, only holes are injected into the organic layer,and the hole mobility may be measured as the only charge carrier in theorganic layer.

Fabrication of electron-only device: A layer of Al was first depositedat a deposition rate of 0.3 nm/s upon a glass substrate (110 nm), thesubstrate having been cleaned by ultrasound in acetone, andconsecutively in 2-propanol, then baked at 110° C. for about 3 hours,followed by treatment with oxygen plasma for about 30 min. In aglove-box hosted vacuum deposition system at a pressure of 10⁻⁷ torr (1torr=133.322 Pa), Host-2 was then deposited on top of the Al layer atdeposition rate of 0.1 nm/s, yielding a 100 nm thick film. LiF (1 nm)and Al (100 nm) were then deposited at a deposition rates of 0.015 nm/sand 0.3 nm/s, respectively.

Fabrication of hole-only device: the ITO coated glass substrate (110 nm)was cleaned by ultrasound in acetone, and consecutively in 2-propanol,baked at 110° C. for about 3 hours, followed by treatment with oxygenplasma for about 30 min. A layer of PEDOT: PSS (HIL 1.1 purchased fromH.C. Starck) was spin-coated at 4000 rpm onto the pre-cleaned andO₂-plasma treated (ITO)-substrate and annealed at about 180° C. forabout 10 min, yielding a thickness of around 30 nm. In a glove-boxhosted vacuum deposition system at a pressure of 10⁻⁷ torr, Host-2 wasfirst deposited on top of PEDOT/PSS layer at deposition rate of 0.1nm/s, yielding a 100 nm thick film. Al was then deposited at adeposition rate of 0.3 nm/s. Each individual device had areas of about0.08 cm².

Photoluminescence (PL) spectra were recorded on a FluoroMax-3fluorescence spectrophotometer (Horiba Jobin Yvon, Edison, N.J., USA).2-Methyltetrahydrofuran (2-MeTHF) (Aldrich, spectroscopic grade) wasused as received. 2 M (2 mg of sample/1 mL of 2-MeTHF) was prepared andthen transferred to quartz tube prior to measurement. Then, the samplewas frozen by liquid nitrogen at 77K. A phosphorescent emission spectrumwas recorded and the highest-energy vibronic band was determined tocalculate triplet (T1) energy level.

Cyclic voltammetry (CV) experiments were performed with a μAuto-labIIpotentiostat (Eco Chemie [Metrohm Autolab B.V., Utrecht, theNetherlands]). All measurements were carried out at room temperaturewith a conventional three-electrode configuration, e.g., a glassy carbonworking electrode, a platinum auxiliary electrode, and a nonaqueousAg/AgCl reference electrode. A 15 mL 10⁻⁴ M HT-1 from 0.1Mtetrabutylammonium hexafluorophosphate, nBu₄PF₆ DMF sample solution wasprepared at room temperature and prior to measurement, the solution waspurged under argon for 5 mins. Then anodic potential up to 1.6 V (enoughpotential to contain oxidation potential of HT-1) A 1.5 V potential wasapplied to this test sample resulting in a test sample oxidationpotential [figure]. Scan rate used was 100 mV/s. About 1.0 mg offerrocene/ferrocenium was then added to the test sample at the end ofeach measurement for calibration and the oxidation potential measuredagain. From these oxidation potential spectra, the E_(1/2) values weredetermined as ½(E_(p) ^(a)+E_(p) ^(c)), where E_(p) ^(a) and E_(p) ^(c)are the anodic and cathodic peak potentials, respectively. HOMO (Highestoccupied molecular orbital) energy was calculated by adding thedetermined shifted E½ value with reference to ferrocene (4.8 eV).

A 10 mL 10⁻⁶M analyte, e.g., Host-1, chloroform (CHCl₃) solution wasanalyzed with a Cary 50 spectrophotometer (Varian, Inc. [AgilentTechnologies, Santa Clara, Calif., USA]). Analyzing an absorption as afunction of wavelength plot provided an observed optical onset (eV),providing an estimated Optical band gap value, Eg (Opt). LUMO (lowestunoccupied molecular orbital) energy was determined from the relation,Eg (Opt)=HOMO−LUMO.

Subsequently, the values for Host-2, Host-3, and Host-4 were determinedin a similar manner to that described in example immediately above. Theresults are reported below in Table 1.

TABLE 1 solution Film em em peak peak HOMO LUMO Tg T1 (nm) (nm) (eV)(eV) (° C.) (eV) μ_(n) μ_(e) Host-1 433 422 −5.37 −2.17 117 2.4 1.65 ×3.0 × 10⁻⁵ 10⁻⁶ Host-2 412 403 −5.66 −2.16 122 2.59 1.3 × 5.4 × 10⁻⁷10⁻⁷ Host-3 401 404 −5.68 −2.15 151 2.72 1.4 × 1.2 × 10⁻⁷ 10⁻⁵ Host-4431 416 −5.64 −2.4 145 2.65 8.5 × 4.7 × 10⁻⁶ 10⁻⁷

8.3 Device Configuration

Fabrication of Light-Emitting Device:

A device as set forth in FIG. 1 was fabricated as follows. The ITOsubstrates having sheet resistance of about 14 ohm/sq were cleanedultrasonically and sequentially in detergent, water, acetone and thenIPA; and then dried in an oven at about 80° C. for about 30 min underambient environment. Substrates were then baked at about 200° C. forabout 1 hour in an ambient environment, then under UV-ozone treatmentfor about 30 minutes. PEDOT:PSS (hole-injection material) was thenspin-coated onto the annealed substrate at about 4000 rpm for about 30sec. The coated layer was then baked at about 100° C. for about 30 minin an ambient environment, followed by baking at about 200° C. for about30 min inside a glove box (N₂ environment). The substrate was thentransferred into a vacuum chamber, whereN,N′-bis(naphthalen-1-yl)-N,N′-bis(phenyl)-2,2′-dimethylbenzidine (a-NPD[hole transporting material]) was vacuum deposited at a rate of about0.1 nm/s under a base pressure of about 2×10⁻⁷ torr. YE-01 (10 wt %) wasco-deposited as an emissive layer with Host-1 host material at about0.01 nm/s and about 0.10 nm/s, respectively, to make the appropriatethickness ratio (about 30 nm).1,3,5-tris(1-phenyl-1H-benzimidazol-)2-yl)benzene (TPBI) is thendeposited at about 0.1 nm/s rate on the emissive layer, yielding a layerof about 30 nm. A layer of lithium fluoride (LiF) (electron injectionmaterial) was deposited at about 0.002 nm/s rate followed by depositionof the cathode as Aluminium (Al) at a rate of about 0.3 nm/s. Therepresentative device structure was: ITO (about 150 nm thick)/PEDOT:PSS(about 30 nm thick)/NPB (about 30 nm thick)/Host-1: YE-01 (about 30 nmthick)/TPBI (about 30 nm thick)/LiF(about 1.0 nm thick)/Al (about 100 nmthick). The device was then encapsulated with a getter attached glasscap to cover the emissive area of the OLED device in order to protectfrom moisture, oxidation or mechanical damage.

Device B (FIG. 2) was constructed in a similar to Device A, except thatTcTA was deposited instead of NPB, andtris(1-phenylpyridine)(acetylacetonate)iridium (III) (“Ir(ppy)₃”) (10 wt%) was co-deposited as an emissive layer with Host-2 host material atabout 0.01 nm/s and about 0.10 nm/s, respectively, to make theappropriate thickness ratio (about 30 nm).

Each individual device has an area of about 0.16 cm².

Device Performance of Device B was evaluated by measuring the currentdensity and luminance as a function of the driving voltage, as shown inFIG. 3. The turn-on voltage for the device was about 4.17 V and 5.34 Vat about 1,000 cd/m² and 10,000 cd/m², respectively. The luminousefficiency (44 lm/W) and power efficiency (60 cd/A) of the device at1000 cd/m² were determined as a function of luminescence (FIG. 4). Adevice efficiency of 17% was higher than expected, and demonstrates thatHost-2 may be useful as host materials in a light emitting device.

Unless otherwise indicated, all numbers expressing quantities ofingredients, properties such as molecular weight, reaction conditions,and so forth used in the specification and claims are to be understoodas being modified in all instances by the term “about.” Accordingly,unless indicated to the contrary, the numerical parameters set forth inthe specification and attached claims are approximations that may varydepending upon the desired properties sought to be obtained. At the veryleast, and not as an attempt to limit the application of the doctrine ofequivalents to the scope of the claims, each numerical parameter shouldat least be construed in light of the number of reported significantdigits and by applying ordinary rounding techniques.

The terms “a,” “an,” “the” and similar referents used in the context ofdescribing the invention (especially in the context of the followingclaims) are to be construed to cover both the singular and the plural,unless otherwise indicated herein or clearly contradicted by context.All methods described herein can be performed in any suitable orderunless otherwise indicated herein or otherwise clearly contradicted bycontext. The use of any and all examples, or exemplary language (e.g.,“such as”) provided herein is intended merely to better illuminate theinvention and does not pose a limitation on the scope of any claim. Nolanguage in the specification should be construed as indicating anynon-claimed element essential to the practice of the invention.

Groupings of alternative elements or embodiments disclosed herein arenot to be construed as limitations. Each group member may be referred toand claimed individually or in any combination with other members of thegroup or other elements found herein. It is anticipated that one or moremembers of a group may be included in, or deleted from, a group forreasons of convenience and/or patentability. When any such inclusion ordeletion occurs, the specification is deemed to contain the group asmodified thus fulfilling the written description of all Markush groupsused in the appended claims.

Certain embodiments are described herein, including the best mode knownto the inventors for carrying out the invention. Of course, variationson these described embodiments will become apparent to those of ordinaryskill in the art upon reading the foregoing description. The inventorexpects skilled artisans to employ such variations as appropriate, andthe inventors intend for the invention to be practiced otherwise thanspecifically described herein. Accordingly, the claims include allmodifications and equivalents of the subject matter recited in theclaims as permitted by applicable law. Moreover, any combination of theabove-described elements in all possible variations thereof iscontemplated unless otherwise indicated herein or otherwise clearlycontradicted by context.

In closing, it is to be understood that the embodiments disclosed hereinare illustrative of the principles of the claims. Other modificationsthat may be employed are within the scope of the claims. Thus, by way ofexample, but not of limitation, alternative embodiments may be utilizedin accordance with the teachings herein. Accordingly, the claims are notlimited to embodiments precisely as shown and described.

1-21. (canceled)
 22. A host compound for use in emissive elements oforganic light emitting devices, the compound being represented by aformula:HT-Ph¹-Ph²-ET wherein Ph¹ and Ph² are independently optionallysubstituted o-phenylene; HT is optionally substituted phenylcarbazolyl,optionally substituted (phenylcarbazolyl)phenyl, optionally substituted4-(phenylnaphthylamino)phenyl, or optionally substituted4-(diphenylamino)phenyl; and ET is optionally substitutedbenzimidazol-2-yl, optionally substituted benzimidazol-2-ylphenyl,optionally substituted di(benzimidazol-2-yl)phenyl, optionallysubstituted benzothiazol-2-ylphenyl, optionally substitutedbenzoxazol-2-ylphenyl, optionally substituted di(benzoxazol-2-yl)phenyl,optionally substituted 3,3′-bipyridin-5-yl, optionally substitutedquinolin-8-yl, optionally substituted quinolin-5-yl, or optionallysubstituted quinoxalin-5-yl.
 23. The host compound of claim 22, furtherrepresented by a formula:

wherein R¹, R², R³, R⁴, R⁵, R⁶, R⁷ and R⁸ are independently H, C₁-C₃alkyl, or C₁₋₃ perfluoroalkyl.
 24. The compound of claim 23 wherein R¹is H.
 25. The compound of claim 23, wherein R² is H.
 26. The compound ofclaim 23, wherein R³ is H.
 27. The compound of claim 23, wherein R⁴ isH.
 28. The compound of claim 23, wherein R⁵ is H.
 29. The compound ofclaim 23, wherein R⁶ is H.
 30. The compound of claim 23, wherein R⁷ isH.
 31. The compound of claim 23, wherein R⁸ is H.
 32. The compound ofclaim 23, wherein R¹, R², R³, R⁴, R⁵, R⁶, R⁷ and R⁸ are H.
 33. Thecompound of claim 22, wherein HT is optionally substituted4-(phenylnaphthylamino)phenyl.
 34. The compound of claim 22, wherein HTis optionally substituted phenylcarbazolyl.
 35. The compound of claim22, wherein HT is optionally substituted 4-(phenylcarbazolyl)phenyl. 36.The compound of claim 22, wherein ET is optionally substitutedbenzimidazol-2-ylphenyl.
 37. The compound of claim 22, wherein ET isoptionally substituted di(benzimidazol-2-yl)phenyl.
 38. The compound ofclaim 22, wherein ET is optionally substituteddi(benzoxazol-2-yl)phenyl.
 39. The compound of claim 22, wherein HT is


40. The compound of claim 22, wherein ET is


41. The compound of claim 22, wherein the compound is:


42. An organic light-emitting device comprising a compound of claim 22.